Time to go or wait? Sailing and coding anyone?

[maplemale]

This is my first post! Some background on myself...


We have been dreaming of living aboard for about 3-5 years now. We - being me, my wife and 2 kids (4 and 6). We are from MT and Canada originally, we live on the OR coast and are pretty tough folks, mentally and physically. We currently home-school the kids. I'm a .NET dev of 15 years for a large company. Me and my wife have worked hard for the last 5 years with the hope of getting the residual income to a point where we can leave and not stress too much about ever coming back unless we want to. We currently rake in about $20-$25k net residual from rental property. That's a conservative estimate after all repairs. We'd pull in another $3-5k yr by renting our current house and we've saved about $120k - $160k so far in cash to buy a boat. I've mostly been looking at 41 - 50ft Beneteau, Hylas etc. in the $120k range. My wife and I are definitely the more adventurous types. We won't be content to live in a slip for 4-6 months a year! We want to sail! We want adventure, trials and rich experiences and we want that for our kids!


And now the dilemma... to buy another rental property with what we've saved and increase our monthly residual, putting off sailing for probably another 3 years or, is it time to get out of here? I realize that might be hard for anyone but us to answer. Maybe someone could help with the things I might not be considering?


I know $25k - $30k a year for a family of 4 is probably not much. But, consider that I am a very experienced full stack dev. Though, I'm 100% .NET - not open source. I've never looked for side work in my industry and I'm not certain how difficult it will be for me to convert to being a moonlighter from my cushy engineering job at a fortune 500 company - a job I quite honestly am sick of. Also, the challenges of coding while traveling in other countries? Realistically, is there anyone else who sails and does part time dev work that can tell me how much time they spend working and how they go about finding said work? Are you also doing all the maintenance yourself (something I'd like to do) or would you rather spend the time working while maintenance is being done? Anyone with experience sailing the Caribbean while working part time? What are your internet / computing solutions? Also, considering my other skills: how likely is it I'll randomly find work doing other things aside from coding? Is $30k a year for a family of 4 on a 40-50ft boat really kind of a joke?

[ur2slo]

Originally Posted by maplemale

This is my first post! Some background on myself...


We have been dreaming of living aboard for about 3-5 years now. We - being me, my wife and 2 kids (4 and 6). We are from MT and Canada originally, we live on the OR coast and are pretty tough folks, mentally and physically. We currently home-school the kids. I'm a .NET dev of 15 years for a large company. Me and my wife have worked hard for the last 5 years with the hope of getting the residual income to a point where we can leave and not stress too much about ever coming back unless we want to. We currently rake in about $20-$25k net residual from rental property. That's a conservative estimate after all repairs. We'd pull in another $3-5k yr by renting our current house and we've saved about $120k - $160k so far in cash to buy a boat. I've mostly been looking at 41 - 50ft Beneteau, Hylas etc. in the $120k range. My wife and I are definitely the more adventurous types. We won't be content to live in a slip for 4-6 months a year! We want to sail! We want adventure, trials and rich experiences and we want that for our kids!


And now the dilemma... to buy another rental property with what we've saved and increase our monthly residual, putting off sailing for probably another 3 years or, is it time to get out of here? I realize that might be hard for anyone but us to answer. Maybe someone could help with the things I might not be considering?


I know $25k - $30k a year for a family of 4 is probably not much. But, consider that I am a very experienced full stack dev. Though, I'm 100% .NET - not open source. I've never looked for side work in my industry and I'm not certain how difficult it will be for me to convert to being a moonlighter from my cushy engineering job at a fortune 500 company - a job I quite honestly am sick of. Also, the challenges of coding while traveling in other countries? Realistically, is there anyone else who sails and does part time dev work that can tell me how much time they spend working and how they go about finding said work? Are you also doing all the maintenance yourself (something I'd like to do) or would you rather spend the time working while maintenance is being done? Anyone with experience sailing the Caribbean while working part time? What are your internet / computing solutions? Also, considering my other skills: how likely is it I'll randomly find work doing other things aside from coding? Is $30k a year for a family of 4 on a 40-50ft boat really kind of a joke?

Everything else will come together, your young, established, how much $$ do you really need to justify a journey thru life?

JUST GO!

[ur2slo]

Oh My apologies...........HI & welcome, lots of info if you garner the good..............

[the_alpine]

With those numbers you will HAVE to do the work on the boat yourself. Why would buying another rental property put you back 3 years? Could you not pull equity out of the current house to fund a down payment on a rental? Sure that would cut your annual return from 1 house by a few hundred maybe 1k, but that would be made up by the new income source from the 2nd house.

If you hate coding now, you're definitely gonna hate it once you're adventuring on the boat.

[UNCIVILIZED]

Go now! You have enough coin, & plenty of income. The one (or two) hiccup with your plan is boat size. Since the costs go up almost with the cube of length. And there's enough room in lots of 40'ers (or smaller) for you & the family. Given that people have crossed oceans, & cruised full time in 25'ers with a family of 4.

There are lots of threads on living frugally, & on small budgets while cruising. Much, much smaller than yours. It will take a bit of getting used to, yes. But also consider that you'll be living in a tiny space, & thus can't buy much, as you'll have little enough room for it.

On the finding work thing. Your primary job will likely be looking after the boat, & the family. Lynn & Larry Pardey break down how much time goes into a cruising boat each year for it's upkeep, & the figures are rather astounding. Not to dissuade you, just being realistic.

Though before you get too far into things, spend some time taking the family sailing, & camping. The kids will likely adapt really quickly, & usually love it. But it needs to be the right thing for everyone. So start small & simple now, working up as you move towards the full time sailing thing.

[barnakiel]

Get into the new style work style / jobs BEFORE you move into the new lifestyle.

Burn no bridges, create safety nets if you can. Keep in touch with you job friends and professional contacts.

Otherwise the time is always now. If something can be done today, one makes some bets when they decide to postpone till tomorrow.

Good luck in your undertaking!

Cheers,
b.

[Hoosiersailor]

If it was me, I would go and go now! If it doesn't work out for any reason, sell the boat and move back on land.

[NoahTreat]

Go. Now

[RickG]

Present a case to your company for sabbatical followed by working remotely. If it does not work out you've lost little. One of my devs convinced us and his client that he could work remotely from Guatemala. Its working out fine.

But, doing development in a couple of hundred square feet shared with young kids? That's tough.

Cheers, RickG

[JPA Cate]

Welcome aboard, maple male.

It will probably help your planning to bear in mind that as they get into their teens, your children will require more privacy than most 40 foot boats offer. However, by starting them soon, your chances will be better for you all creating the private space you will need.

Also, if there is a possibility of your kids being headed for university, one drawback of home schooling is lack of preparation for competitive examination. Cruisers with kids sometimes address this issue by staying in a country and putting their kids in normal schools for a semester or two, or a couple of quarters, depending on how the country's educational system is set up. Often the home school students are more advanced for a particular year than the public school children.

Surviving off rental properties can be done if you have good property managers. We have seen a few cruises ended rapidly because someone had to go "home" to take care of mis-managed rental properties. The further from home you are, the more costly and fraught with stress such voyages are.

Over all, I think it will be easier for your family to cope with less $$ if you start sooner, so, what I say is, start educating yourselves now, and for goodness sake, see if you like sailing and how everyone copes relative to sea sickness. Imho, you have a whole lot of practical considerations you haven't yet expressed to us.

Ann

[maplemale]

Thanks for all the replies! Some good suggestions here... starting moonlighting now and speaking to my company about a sabbatical right before leaving... Both really good ideas!


My wife and I love the water... but our kids haven't been out at all except on lakes. That's probably a good suggestion - to get them out on the water a bit first. After all, they've started developing little personalities and opinions in recent years! Last night we were talking about options to do day sailing while still working - since we live near Newport anyway. The Yaquina bay yacht club appears to have Catalina 25s we could take out for the day... are Yacht clubs generally ok with members who don't own a boat and just wanting connections and to use the club boats for a while?


To answer questions about the houses: We buy all our properties on credit with the goal of increasing cash flow with each. We only buy stuff that cash flows a good 20% or more over the payment from day one. Most of our properties are about 50% LTV, though the latest one of course is not. If we bought another one (instead of a yacht), we'd be increasing our cash flow by maybe $300 - $600 a month more but likely eat up most of the savings to do it and having a good 6 months of remodel, finding a new property manager for a new state etc. They are all out of state and we don't manage them except for one that's a vacation rental. But, we got lucky and have an astounding manager for 3 of them who literally takes care of everything at 8.5% rate (due to having multiple).

[donradcliffe]

One other reason to go now is that home schooling is fine for now, but the kids will probably be happier and better off in a high school setting when they are in their teens.


The best time to find another job is while you are working, but I got several offers after i quit and went sailing. I actually came back and worked for a while three times, and the hardest decision was quitting the first time.

[maplemale]

Originally Posted by donradcliffe

One other reason to go now is that home schooling is fine for now, but the kids will probably be happier and better off in a high school setting when they are in their teens.


The best time to find another job is while you are working, but I got several offers after i quit and went sailing. I actually came back and worked for a while three times, and the hardest decision was quitting the first time.

That's interesting... about quitting and coming back. I've always been of the opinion, once I quit, I'm done. But, maybe I'd change my mind later. There's always contract work. My concern is internet access.


Regarding homeschool and as someone who was homeschooled k-12, I'm not sure I agree. Not sure I entirely disagree either. I think it depends on the kids. But, I think you're right in saying - easier now than later for many reasons.

[rwells36]

Have you considered a trawler instead of a sailboat? If you have a goal to be in the Bahamas area I definitely not buy a west coast boat; buy it in FL. A trawler has more room and; in my opinion is less work.

[Byrdman]

You could always start locally with a smaller (cheaper) live aboard but big enough to leave for a few weeks at a time. Plus once you decide to pull the trigger, you would be able to pick up side jobs while cruising in your line of work. I would think once your development reputation gets around in the carribean, you mind find more work than what you want.