Well I have been trolling Craigslist for a used pop up. I want to get one so my son and I can go camping. My parents took me and I remember those vacations more than Disney vacations we went on. My son is six and just loves being outside. I just wanted to see if there was anything I should look out for or brands to get or stay away from or just suggestions in general. I don't really want to spend more than $2,000 to $3,000 and want to be no older than year 2000. I have seen some like that locally on Craigslist but have not made it out to look at any as of yet. Size doesn't matter but I wouldn't mind a smaller one just less to take care of and since it will be just my son and I we don't need a big one unless the price is right. I have a full size 3/4ton pickup so towing isn't a problem. let me know what you think, thanks in advance.

I have a small rockwood. It has been fine  join the popupportal forum

I have one sale. Sorry, I forgot about not posting for sale ads. If you are interested , message me

Have you considered tents?

A good tent is an option.  Especially if you put boating and fishing into the mix.  That way you can tow the boat.  Pretty much why I never got a tow behind camper of any type.  Heck even hunting sometimes I take a boat to go across a lake to backwoods public land.  

A good tent with a good rain fly, another rain fly over a picnic table and you can get well on.

I will say the only reason I got a pop-up is for the family.  My wife wanted a camper. It has a.c. and that makes them happy. But a pop-up is really only a tent with a hard roof. My daughter loves tent camping though so if I sell mine it wold only be to upgrade to a little more room or maybe just pocket the money.

Get a fifth wheel camper, then you can tow the boat behind that

Even just a large blue tarp and some rope can make a nice rain fly over a picnic table.

Don't  let the neigh sayers discourage you. We had a Rockwood popup that was nice. Towed it to Florida several times and as far north as Nebraska.  A/C, water heater, shower, potty. Slept 6 comfortably. They are easy to tow and park. Easy to back up and can fit in your garage. We moved up to a 34 foot bumper pull that I sold with in a year and bought a hybrid. Basically a hard sided pup up. Kinda best of both worlds. I hated the large travel trailer and really miss my popup.

This one has three beds that fold out and a slide out. Zero floor space is taken up by a bed.

The AR15com of pop-up sites- http://www.popupportal.com/index.php?action=forum

No brand-specific recommendations; my parents have one and love it for summer but I have no idea what kind.
General advice: check the canvas and the plywood under the slide-outs very carefully. Plywood isn't expensive to replace but kind of a pain. Canvas can get spendy in a hurry.
Ask the seller to show you how to put it up and take it down BEFORE you agree to buy. If they're showing it all-set-up then there might be a support that doesn't quite fit right until you jiggle it just so and kinda kick it and wedge your shoulder against the side and... or something along those lines.

I'm starting to look at/into teardrop campers; all I want is a good roof over my bed and the rest of the time I can be outside.

Some friends of mine ended up finding a heck of a deal on a coleman brand popup and it was surprisingly well built. They had some small TLC things to work on but I was impressed with it.