Hey I think the Bristol 38.8, Little Harbor 38 & the Wauquiez Hood 38 are all very nice boats. But I think they are getting out of jerrycooper14 original budget of around 65,000 ?..... Unless I am wrong.....I think you would be hard pressed to find one under $85k (Unless of course it needed a little help....)
And I think everyone is getting away from his initial desire to find a boat to live aboard and coastal cruise in the Keys/USVI NOT around Cape Horn. And since this is his first boat I don''t think he needs one with a PHRF rated under 100. Also there is *nothing* inherently wrong with a simple
rig that has a mainsail w/overlapping genny. And with the right boat I wouldn''t say that they are hard to singlehand (Unless they were overcanvassed). On the contrary a little heavier (D/L) boat with this setup can be easily singlehanded albiet with a less than exciting light air capability. A lighter boat that "sails on her ear" and very bendy spars might be the ultimate singlehander for a very experienced sailor . But how much experience do you have with "tweeking" your mast on the fly?... Do you have experience with running backstays? How about a backstay adjuster? Do you understand the dynamics of tuning these under sail in different conditions? Who knows, you might be doing more harm than good?
I think for most sailors, simple is better. Get a little heavier, simple, stable boat. You will sail more comfortably , maybe a little slower in light air. But after a few years if stellar performance is what you are looking for and you have the funds available, then you can move into one of the more "performance" orientated boats.