Mac,
Welcome! Getting started with sailing after
power boating isn't that hard since all your experience is not to waste. All your time on the
water is a valuable thing to have behind your now. Nice to see your wife got you the
ASA series of
classes. They are a good way to start. Bring your wife along too. It's worth it. She will learn a lot and it's just going to ensure you both have fun. It's perhaps the one thing to always be thinking about. It is all supposed to be fun.
Given your ability to keep a boat is limited for a period you might go ahead and
work through the ASA courses, then do a
charter or two. Getting more time on the
water is probably the best use of your time in between. Sailing your uncles boat sounds like a plan for a bit as well.
Miami Strictly Sail is next month. If that took you two years then you might be in a better position.
Your
budget is going to
work more along the lines of the 34 ft boat. The
concept of space below is perhaps the one change you need to consider. To get the queen centerline berth with
head room just doubled your annual costs plus killed the
budget. Having one serious requirement like that dictates a lot of other things you might not want. It means looking at a lot of the details in any boat you consider. Center cockpit boats don't get all that efficient with space until you reach about 44 ft and many of those don't work well. Annual costs will be an issue once you start getting that large and your plans really don't require it.
If you are used to
power boat maintenance then I would say
sail boat maintenance isn't any less but includes some additional
gear and a smaller
engine. The difference between a 34 ft boat and a 40 ft boat is not just 6 feet. Having made that step a year and a half ago my back tells me it's a whole lot more. For weekending and marina hopping with perhaps a week or two you can actually do it with a 30 ft boat and have some comfort. You will probably want more though. Your use is looking more less
displacement (you are not hauling tons of supplies) probably in the 33 to 36 ft range. I think the Catalina 34 in an older Mk II design might fit the budget and the goal pretty well. There really are a whole lot of different boats in this range. I think you'll do better at least starting form there and looking at more boats.
Better yet work on getting aboard a few more boats and perhaps even a
charter. Familiarity starts to make boats feel more comfortable. You really are going to need the Admiral along on all this too. The transition from
power to sail changes the shape of the boat and the
head room drops until you get into the really large boats. It's the hard part of getting used to a different style boat. Strictly Sail
Miami is just around the corner.