Re: Looking for a cruiser
I'll try to give some perspective as you're exactly where I was 1 year ago.
The criteria, after beginning as a 22' or so cuddy, morphed into something that could sleep 4 and carry 8 but was still tow-able. In the US that generally means 8'6" beam or less so that was a key limitation. Like you, I was a first time boat owner and really never even drove anything bigger than a 20' open bow. We mainly go in the rivers and small lakes here in PA.
We went around the Great Lakes region and looked at several different boats. I wont get into too much detail on that except to mention a couple you might be interested in. The Four Winns vista 258 / 248 were nice and either would've fit the bill nicely, though the 258 was a bit roomier. We also looked at a Wellcraft prima 243 which was in the same class and seemed like a well made boat. I never got to see a Sea Ray but the layouts looked nice.
We ended up going with a Crownline 250CR. Its a single 7.4L with a bravo II drive. We got a 95 model but I understand the 98+ used better plywood. Like others have said, expect to fix things on a boat this old. I fix everything myself if I can so I wasn't too put off by this, but be aware of it. The worst issue I have with it is that there is rot in the deck above the aft cabin from where the helm seat bolts on. I'm going to fix it this year and it shouldn't be that big of a deal. We did have it surveyed and the rest was sound and the price was right. I did some work on the water and waste systems but nothing that anyone who can do their own household plumbing can't handle.
A short summary of my experience / lessons learned 1yr in.
#1. It took up every weekend. 1/2 working on it and 1/2 using it. I expect it will be like this next year too until all the issues are worked out. We trailer rather than slip, and will for the foreseeable future because working on it is much easier in my driveway than the water.
#2. I tow with a diesel F350. I think you could tow with a 1/2 ton but I wouldn't want to go very fast or very far. If you're in mountains that won't be a good combo.
#3. Launching is easy, but retrieving these things is dicey and not a 1 person operation. It took the whole season but the wife and I are finally getting the hang of it. Be prepared for a learning curve.
#4. Docking is easy, especially on the starboard side. Don't be intimidated or think you need twin engines. I routinely dock and tie up by myself.
#5. Engines: The 7.4L is enough power, but it isn't fast (~40MPH top speed). I'd expect a 5.7 to be downright slow.
#6. Props: I was looking for a bravo III or volvo dual prop. After whacking the prop twice this year I'm awfully glad I got a single, fixable aluminum prop.
#7. Power trim tabs: Get 'em.
#8. Gas hasn't been an issue. I use about 30gal in a long weekend, if we don't run around all day or pull people.
#9. We love sleeping aboard on the hook, and I wouldn't want a boat I couldn't do that on. 3 days is no problem. That being said the Crownline has a very big cabin and a smaller cockpit and if anything I feel like a larger cockpit would've been a better use of the space.
#10. We got a full cockpit enclosure (camper style). This has been a key feature. We rode out several storms comfortably with the canvas up, and one very uncomfortably when I didn't get it up in time. Now thunder = canvas.
#11. Another key feature has been the pump toilet with holding tank. I can't imagine a portable after 3 days aboard. Because there aren't pump stations where we boat, I got a "waste caddy" which lets me pump it out myself when I get home. I use enzymes and usually let it sit a couple days before I do it and it's not too bad.
#12. When shopping don't overlook the trailer. Mine needed lots of work that I didn't catch even though I was looking, and I had to get the boat off to do it which made it very inconvenient.
#13. Storage can be expensive, so consider it. Around here we have limestone mines. $60/month, humidity controlled and a constant 54F. Can't beat it, but our boat is about the biggest that can get in there.
So far we are happy with the boat and are looking forward to using it more often. This post ended up long enough and I'm sure I missed things but I hope this helps you make a decision you'll be happy with.