Short list

[camaraderie]

Jeff...sounds like you plan to go cruising rather than weekend sailing. You are right...35' is small these days for a cruising boat for a cruising couple. Most SSCA members have boats in the 40-45' range for good reason...and 50% of them have CC boats for the reasons you cite. Dawg quotes Beth Leonard on the forces between 35 and 40' boats. Interestingly, she sails a 47' boat with her hubby in some really wild places. We sailed a 52'CC quite comfortably through the Caribe.
When you are living aboard full time, the boat is your HOME...it needs space and comfort and the ameneties that make it right for you rather than an extended camping trip. The Hylas44 is a good choice for that.
Have no fear about handling such a boat as a couple.

This is not to say that people can't cruise happily on a 35 footer...just that if you can afford it...a 44 footer gives you the ability to be safer at sea and more comfortable at anchor.

[sailingdog]

Beth's points were that the smaller boat they had was a much better first boat, and far more forgiving of the mistakes they made while learning to cruise. Leonard also points out that their new, larger boat, requires them to have better seamanship skills than did their smaller boat, because it is often less forgiving than the older smaller boat would be, given the same mistake.

[bestfriend]

BigJeff, if you still want my help please let me know! Was waiting to hear back from you.
Best

PS you are right about 35' being too small. I have 34' and I need more to be comfortable after a few days. Having a 9' surfboard on board is no help either!
As far as singlehanding goes, its not harder to go bigger if all the rigging is set up properly. The hard part is docking and mooring and of course rough weather sailing will be more difficult.

Also, the advice by the members above is very sound. Lots to think about. A lot depends on your abilities. While you have lots of experience on the water, do you have lots of sailing experience. Depending on your cast off date, you may want to buy something around 27-30' first, get all the basics down, learn how to do repairs on everything, get real proficient at single handing. Then after a year or two, put her up for sale, expecting it to take a year to sell, and start looking bigger.

[bigjeff]

Yes bestfriend if you could check it out.
Delamination obviously a big issue.
And general condition.
Sorry dont have enough posts to get back to you.
Will try over next few days to get to 10.

I have several years of sailing smaller boats and sailed mid size boats al summer to get use to handling larger boats.

Thanx Camaraderie and Sailingdog great advice!