Re: I'll start here ......
I think you're leaning in the right direction. A Trawler/Cruiser will afford you a lot more room to live aboard and it will be a little easier to get the hang of. None of them are "rocket science", of course, but there's a lot to be said about turning a key and going, regardless of the lack of wind.
Width or beam of the boat has been mentioned and I think you'll find that it makes a huge difference in the amount of room. Keep that in mind while you're internet shopping as it will be obvious when you're shopping in person. And yes, folks will show you their survey, most of them might even want you to stop there, lol.
Your budget should afford you a nice boat and an incredible "starter boat". Take your time as there are plenty out there, and that number will increase, depending on the area of the country you're looking in. In other words; the frozen tundra, which to me is anything north of Georgia...buwahahaha. By all means, make sure you have both a survey AND a mechanical survey because they're usually 2 different things. That doesn't mean that one guy isn't capable of doing both, but that you need to have that discussion prior to an inspection. It's the hidden things that can and will hurt you later on.
All in all it sounds like you've got a logical head on your shoulders and for being a "newbie" are pointed down the right path. The only thing I might add is to consider re-sale when purchasing, just in case you decide in 6 months it's "not for you". Spending a little time researching specific models will help clear up any fogginess in that arena. But from a basic standpoint: just because it's attractive to you, doesn't mean that anyone else likes it. Knowing that, invest your money in the things that ARE important to any future buyer: motor, electronics, hull condition, etc. etc. etc. Good luck!