Re: Trailer sailer
First Brad let me apologize for assuming you were trolling... You've since figured out why I would think as much (the Mac 26x, the motorsailor is a HIGHLY polarizing boat).
So lemme first properly welcome you... and let me say that, sailing can be the most difficult sport challenge, but life altering, and still enjoyable hobby/sport/addiction you could ever endeavor to try. For that, I say "welcome to the addiction!"
As I see it you have several different requests ALL in conflict with one another. Please fix/ammend my comments below... if I read wrong:
* You have a Jeep (assuming cherokee/Grand not wrangler) that can tow #3500 - my assumption then is you want trailerable (as is also your topic headline)
* Your wife is uneasy about water time (not unusual by the way).. this needs more definition, is it the water (can't swim) or boats, or worse sailboats (heeling), others will chime in on how EASY it is to assuage fears in that category
* Because of above you want live-aboard, or camp aboard accomodations, as "bigger is better."
* You want to do what amounts to short open water crossings...
* You have roughly $15k to throw at this (assuming all up, meaning maintenance and fix its, for the first year or 2)
Broken down like this, I'm going to tell you right now, you aren't going to cover all those bases. Regardless of what you'll do you'll wind up with a compromise boat. ONLY YOU can figure out what priority list you have from that list above.
Several will tell you the Norsea 27 is a trailerable, bluewater, headroom cruiser, that fits MUCH of your requirements... but you aren't towing it with your Jeep, nor are you likely to find a servicable one for $15k.
A Capri 18 will have a porta-pottie, is trailerable, all up package is exactly #3500, but it's hardly comfortable below, nor capable of much if any offshore work.
So it's decision time... Because most here will tell you, a boat slip at $2500 a year (guess), and heavier boat for a light offshore day sail for under $15k for the first year is POSSIBLE (yeah the market is THAT bad), but of course it'll not be towable except with a crane and a diesel pickup.
Now as for the Mac 26x... I don't think it's a bad boat (there I said it)... I do think it's a compromise boat. Having a 50hp motor especially an outboard, is hardly a "safety factor." At least no more than a 9.9hp outboard would be, and most will tell you a good inboard is a better choice for any harsh conditions...
That being said, I'd LIKE to help you prioritize your list (as it sounds like most here would as well)...
If you REALLY want this to be a hobby you and your spouse can enjoy... you MIGHT want to invest in ASA classes for you both! Might also be better if you take the classes at different times, so you are not there to shadow her. Once she has a handle on what makes the boat go, and stop, and does some actual driving of the boat, she MIGHT be less afraid of the water (assuming the fear is not the water it's the boat).
If there is a fear of water in general (say she cannot swim), then swimming lessons perhaps... but that's not likely gonna help as much as you might think. If it's just the open water, then perhaps you might want to rethink doing this together! I know I am really throwing a monkey wrench there.. but Honestly you cannot compel your spouse to like your hobbies, and sometimes its better to not try to go down that road. What happens as you expand your hobby is you build a resentment towards your hobby if the spouse doesn't enjoy it for themselves, but instead enjoys it for YOU! Sorry, some spouses won't ever enjoy it for themselves.
NOW, I have a solution to above, at least to an extent. Sometimes they get over the fear of "sailing," or "the water" as you become a more competent skipper. You can do that by getting miles (nautical of course) under you belt in various weather. Then you can ease fears by sailing "flat" and picking short destinations for whatever THEIR favorite things to do are (say antiquing, or shopping, or laying at the beach, or just browsing historic sites)... So now the boat is a mode of transport, not the hobby. If that "grabs" the attention, it can turn YOUR hobby into HER hobby, if in an indirect way... but that is a HUGE stretch, and its hard to get there.
So Step 1. Classes for you both if you can.
Step 2. Get a small boat for YOU to cut your teeth, and put it where you can get the most "tiller-time" 2-3-4 times a week is best.
Step 3... Decide what size boat will get you where you ultimately want to be (by then you'll know if it's with the wife or not).
S2 7.9 - cheap, fast, trailerable, and paid for.