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?