First time REAL boat owner checking in ----
Take every opportunity possible to get out in other peoples boats. NOW, Heres the process I went through that totaled up to about a year worth of thinking, list making, browsing...
What can my tow vehicle handle? The truck I had at the time was sufficient to haul any boat I was interested in.
Price range? I decided I was wanting to get in something for around $6-10k. I changed that later on though and I will get to that in a bit...
What kind of water will I fish? HP Restrictions? Will I be wanting to move from small lake fishing to big lake fishing? - I concluded I wanted at LEAST a 90hp on whatever boat I got. One of the lakes I love fishing has a 50hp limit, so I had to nix that lake off the list. I found myself more intrigued getting into big lake fishing and river fishing, so I decided I needed at LEAST the 90 hp.
Aluminum or fiberglass? I decided on aluminum after I read Mike Iconellis book - he talks about winning his first glass boat and slamming it pretty hard into a dock when he is launching it, thus breaking a decent size hole in his hull. I knew I'd be getting into a learning curve solo boating with a legit boat, so I chose aluminum. Good decision on my part.
What kind of setup do I want? Console steer or stick steer? I went with console
What amenities are a MUST have? Storage? 4 stroke engine vs 2 stroke? Graphs? rod lockers? My only MUST was decent storage. After getting my boat, I'm really happy it has an 8ft rod locker capable of holding around 10 rods.
New or used? Obviously, you're like me and going to be looking for used... so that brings us to the next point....
How USED is okay with me? I decided I was fine with mid mid 90's til current models so long as it was in decent looking shape. I looked at quite a few boats and walked away from all of them because there was something just not right with them. Crappy interiors, super dinged up hulls, just old and unkept stuff...
Keep an eye on craigslist and see what boats you like are being listed for in your area. In my $6-10 price range I was finding stuff similar to what I wanted, but all of them were coming up in poor condition and just lacking something.
After eyeing craigslist for months, I ended up going to take a look at a few boats and take them all out. I passed on all of them because something was just wrong with them. I got discouraged and decided I'd be willing to go up to $19 to get into something close to brand new that wouldn't give me any major problems for a long time.
Ended up in an Xpress h-18 with a 150hp for $19 about 2 weeks later. Love it still to this day. Great boat.
NOW - bear something in mind here - Almost no matter what boat you get into, inevitably you will want "more" after fishing out of it for a period of time.
With all of that out the way, it seems like you're just interested in getting a john type boat. Mid 90's Tracker boats go from around $2,000-$3,000 in my area with a 50hp motor. Great boat and good for smaller applications and can handle big lake/ river fishing to a degree. That was the first boat I bass fished out of and would highly recommend those. Or, ya know, a john boat with a tiller and a ply-wood deck is another good option, just not really going to be suitable for bigger applications.