Should I sell my truck for a Ford ranger?

buy something built in this century

Yup, sounds like you should sell that money pit and get a 4 cylinder Ranger.  That way you can start doing your own maintenance since its much easier to work with and you're just starting to learn about mechanics.  As a first car, the F150 is a bad choice, its big and it old.  If anything goes wrong ( and things will go wrong for a car that old ) its gonna cost you big money.  

You're still a kid, you need something reliable, cheap, and easy to work with.

The 2 valve engine is so much better to deal with than the 3 valve boat anchor, so the mileage on that isn't awful, can expect 200K+, but yeah, the tranny can drop out on you. I'd make sure the filter and fluid were changed and sort of hope for the best. Personally, I think you're upside down on the truck's value, where I'm at a 99 4x4 F 150 might get $2800 tops on a good day unless it's pretty special. 

I like the idea of getting a 5 speed Ranger with a 4 or 6 banger, even an older Ranger is easier to work on, most of those smaller Ford/Mazda engines are rock solid (till they do implode) and there are millions of them. I have a friend who has owned several 4.0 powered Ford and has never had major issues with the engines. 

What always concerns me is rust on older vehicles from the midwest and some places back east (I'm in Eastern Washington so no salt on the roads) because even the frames can be rusted through to the point of being dangerous to drive. 

I have a 55 F 100 project, I'll be coating the frame with a POR 15/Chassis Saver style product when I start putting it back together; I'd suggest something like that on any truck frame you decide to retain. Luckily trucks do have a body on frame build so you can do a lot of that stuff where-as a newer uni-body car with rust issues is hard to justify doing major work on. 

I hardily agree on selling the 99 F 150, I might look at doing a Vortec GM/Chevy 1/2 or 3/4 IF you need a full-size truck for ease work and better value, BUT I don't like the S10 or Colorado style small trucks because they don't match up to the Ranger, which is dang interesting. 

You do understand that you will not come close to getting $3,200 for your current car now, right ?

99% of pickup truck owners never need what a pickup truck offers. They're just morons.

Rangers are nice to have but won't stand to the power of a F150 F250 or F350 as the ranger only has a 4 cylinder engine and front wheel drive. It can still haul stuff and even has a hitch. It depends on how much serious trucking power you want.

Well friend you know that it is inevitable that something expensive is going to break down on an older vehicle sell it while you can get what you can out of it and get yourself a new vehicle.

i would if you want to