Welcome aboard Captain Starbucks,
Ok, here goes. If what you want seems not to exist it's because it either shouldn't or can't. Any boat designer or builder is going to build what the customer base will purchase, niches in the marketplace are soon filled as they're discovered. I encourage folks to ask why they can't find what they want and identify the parameters that seem to be the sticking points.
There are three main design aspects to any boat: comfort, speed, and economy. You can have any two...but not all three.
Treat finding a boat like choosing a vehicle. I don't know of anyone (personally) that walks into an automall and tells the salesperson "I want to buy a car" with no idea of what they think they want. At the very least define the genre; in the auto world that would be like an SUV, or crossover, or minivan, or sedan, or sportscar, or pickup, etc. Boats come in as many or more genres and without identifying what you want it makes it really confusing.
The first two parameters that are usually defined when designing a new boat are length and speed. Length because it usually sets up where the boat will fit in the market, whether or not it can be towed, and about how many folks can be aboard. Speed because it's the primary parameter that the designer has to deal with; the shape of the hull has everything to do with the target speed and very little else (we're talking about powerboats here, sailboats are different). That's the most important thing to remember when looking at an unfamiliar boat...the designer had some specific speed in mind when drawing the hull lines and to ignore that is to end up with a boat that doesn't do what you want it to. Find out what that speed is if you don't already know.
Speed costs. Period. There's no way to go fast on the water cheaply (leaving out small hydros and such). You must identify the cruising speed that you find acceptable whether that's 6 knots, 15 knots, or 20 knots (anything higher than that is an fairy tale (for cruising) unless on flat water). Remember that water is very dense and power required rises (with speed) in an exponential manner. Choosing your specific cruising speed rules out a lot of boats right up front. Be honest about this. You may want to cruise at 20 knots but if that boat is not small and light (CD22 or the like) it's going to require a lot of expensive fuel to cruise at that speed. There's about 1/3 difference in fuel burn between a modern diesel and a modern EFI outboard (horsepower for horsepower). That 1/3 difference will rarely (if ever) pay for the difference in costs (upfront and maintenance). There are lots of really good reasons to have a diesel powered boat but unless you're choosing a displacement speed cruiser or operating several hundred hours a year fuel savings is not one of them.
A deep-v hull (any deep-v hull and I'm not picking on them) is, by definition, a performance hull intended for high speed operation (that's why they were developed in the first place). Unless that's what you're after don't choose one. Many folks do (because they don't understand the choice) and get frustrated when they can't slow down to more cruiserly speeds or have to use more fuel than they like. Not everyone though, for some folks it's the perfect choice but in the cruiser world (as opposed to fishing world) it generally isn't the best all-around choice. Just as a Corvette is typically not as good a choice for most of us as a standard sedan, crossover, SUV, or whatever. It's a fun car to drive but it doesn't (for most) make the ideal choice for an everyday vehicle.
If you're on a boat under 30-feet (my arbitrary threshold) you're camping. The smallest boat I'd choose to accommodate two couples on a multi-day cruise is a 32 Bayliner. Anything smaller requires a high degree of compatiblity. Cruising with family (usually) is easier. Trying to accommodate two couples on a 25 to 28 footer is very difficult since there will never (usually) be two fixed berths so someone is going to sleep on an uncomfortable convertible dinette or setee. And there will be one small head compartment.
I have a Tolly 26 (which is really 26' 11") and in my opinion it's the Gold Standard of cruising boats of that length (the Commander 26 is also right up there). It has a huge v-berth, a large galley, a large (read usuable) head compartment, a large dinette, a huge cockpit, and a flying bridge. It's great with 6 to 8 aboard for the day but it's best at night for a couple. It makes a lousy trailer boat since it's 10' wide and weighs about 9,500 to 10,000 pounds (without trailer). The one I have is powered with an EFI 350hp gas inboard (fairly new with less than 200 hours on it). It is not an economical boat to run over displacement speeds. At "cruise speed" (15 knots) I get 1.6 nmpg. Ouch! That's at least $40/hr at the moment so it stays at 6.5 knots most of the time (which makes the 350hp engine pretty useless; 50hp would do it).
I bought it at the time because it seemed like a good combination of compromises. Reasonable speed, great comfort, and reasonable economy (including purchase price). The ecomony part has changed because of rising fuel prices and that's changed the balance of factors. The Economy parameter has changed so much that it now seems (to me) out of balance with the Speed and Comfort paramenters so it no longer fits my needs as it once did. Things do change.
Smaller is better. The use of a boat is usually inversely proportional to its length. Choose the smallest boat that will meet your needs rather than the largest you can afford to purchase. There are always exceptions but they're just that...exceptions. Even with my experience with boats (towing them, handling them, launching and retrieving them) I'd use a smaller boat far more often than my Tolly 26, especially if I was trailering.
I owned a semi and trucked for a number of years so I'm pretty comfortable with large rigs. I just towed a Rosborough RF246 (27.5' long) 4,000 miles from Halifax back to WA and it's 8.5' wide. I would not have liked towing the Tolly 26 at 10' wide a lot of the places (like I-90 in Chicago) I travelled with the RF246. Personally the widest I would go for for relatively routine towing would be 9'; that's just 3" per side wider than an 8.5' boat and while it makes a difference it's not too bad, more than that is a pain.
All of this is supposed to be encouragement, please don't take anything as being negative or unsupportive of your search.
Sit down with a pad of paper and really hammer out the things you need. Put "must haves" in one column, "would like to haves" in another column, "would rather not haves" in another, and then "won't haves" in the last column. Get it in writing. Then you can start to balance things out. Having a 27' boat that sleeps 6 and gets 10 nmpg at 25 knots might look nice on a wishlist but it isn't going to happen in reality and if you have your list you make you'll soon see what really might work for you. Trying to keep it all in your head and remember all the boats and then balance it all out is just confusing to the nth degree. And if it's in your head, and not on paper, your emotional brain has easier access to it and can "talk" you into things that might not be the best (been there, done that).
Finally, choose a boat for 90% to 95% of your use. I see folks make this mistake all the time. They'll look at a boat that meets 95% of their needs and desires then decide they need something else to, say, accommodate 4 people instead of 2. When I ask how often that happens they may say someting like once or twice a year when the kids and grandkids visit. Really? You're going buy the larger, more expensive and expensive to run, and more difficult to tow boat that requires a larger tow vehicle so you can accommodate more people twice a year? I suggest to them that they buy the boat that really fits 95% of their needs and then charter a larger boat twice a year when family visits. And they can get a nice 42-footer with two staterooms and two heads and everyone enjoys it more. It's actually the less expenisve option in the long run.
All the best,
Les
