Going for it... A safe way to proceed?

[cbcat]

Hello,

I'm new to the forum (though have been perusing SailNet for some time now). Someone there suggested this site and I'm glad I found it...what a terrific resource.

Here's the quick and dirty... I'm 34 and am ready to get on a boat for 4-6mo/yr (ultimately working towards a f/t cruise). While I've been on boats in various times in my life and feel very comfortable sailing I have very limited practical/instructional experience. I was in the Grenadines this past spring on a 38' cat building time on the water and getting my ASA101. It's a start, but only that.

I am seriously looking into buying a cat to keep in the carib (no charters) and sail as often as work and finances will allow. I have been looking at 38' - 42' cats and am assuming that I will be learning to single hand the boat. I am anticipating having a captain with me until I am safe, confident and comfortable handling the boat on my own.

I'm a person who really jumps into things feet first. I have a burning passion for sailing and the ocean, but having said that...safety is paramount. I think I'm a pretty well rounded, grounded individual (not looking to do anything rash) and certainly looks to do the homework before proceeding on any adventure.

The million dollar question... AM I CRAZY?

Continuing...

I'm trying to get a realistic financial picture as to what this whole venture will cost me. I know there are numerous variables to this question, but trying to get a rough idea so I have a starting point. I'm not a lavish, big spender and can be quite content living a simple life. Still, I'm sure there are plenty of meals/drinks ashore with the occasional entertainment/tour that tend to add up... Here are some monthly basics to start with:

Insurance
Management (when not used)
Repair/maintenance
Upgrades
Cruising budget

...and so forth! Quiet overwhelming for someone new to the whole scene. My personal take is K.I.S.S Being this would be my first boat & p/t cruising experience, there's no reason to get into a boat that's over my head in terms of complexity and cost. Over time I assume I'll step up into bigger and more complex boats, but what I need now more than anything is time of the water...EXPERIENCE.

As we both know all the gadgets in the world can't buy that, so I just need a nice, clean simple cat to log some good mileage in the carib for now. Clearly there are some 'bells and whistles' on my wish list, but those are mostly for safety, nav, comm etc (especially for being singlehanded).

Any ball park you can give me on overall monthly expenses if you assume a debt service of $1500-2000/mo? I think I'd prefer to keep the boat (when not in use) down south ...probably Grenada. I haven't the slightest idea of what to expect in terms of costs for putting it on the hard and related services.

Thanks in advance (sorry for the long post)!