Well, I learned to drive in my grandpa's 68 F-250 but my first car was given to me by my grandma, a 1996 Geo Prizm. I'm the product of a working single mother, so Grandma was the stand in whenever Mom got called in to work a 12 that wasn't on her schedule. I grew up in Wisconsin in the back seat of that car, by the time I started driving it was nearing ****-box territory. The exhaust was more cans than pipe and the rear strut towers were so rotted out you could feel the coilovers shift every time you hit a bump too hard. I'm a fairly young guy(26) but I'm a very old school gear head, machines make more sense to me than people and I think that car helped me grieve a bit when Grandma passed away at 91. That little car drove me through high school and trade school, and when I got out of trade school and the only job I could find in my trade was 72 miles one way, it did that too. I did that drive in that car for over a year, when the head gasket finally gave up it had 359,000 something miles on it, so I donated it to an at-risk youth facility. My first Ford and first truck was an 86 Flareside I bought for 1500 bucks from this guy out in the sticks that should never be allowed to work on vehicles EVER, by the time I got it all fixed up I loved that truck like it was my child. I got 4 good months out of that truck before I got in a head on at 60 mph with a woman that was texting while driving on KY-109, the truck was totaled. When we hit my Bullnose rode right up the front of her Altima and stopped at the windshield, twisted the frame about 12 degrees and snapped both I-Beams in two. I think the fact that I was able to go to work the next day is probably part of what solidified me as a lifelong guy.

Since the Flareside, I've owned two Bricknoses (both 91's) a 2000 Lincoln Town Car, and my current 92 OBS. One of the bricknoses was a bone stock 91 F-150 2wd with 5.0L and AOD. I got over a year out of that truck before it threw a rod, I'm not outfitted for engine swaps and at the time my take home between all the gas (still working 72 miles away) and getting gouged on income tax as a TN resident working in KY was about 300 bucks a week which ruled out going to a shop. So, that truck got traded for some things that go bang. The second bricknose was also a F-150, but it's a 4x4 5.8L with E4od that had already been heavily customized by the PO. We're talking DIY electric fan, 15x14 wheels with 35's, Rough Country lift, etc. I've owned that truck for 2 years and I've heard it run 4 times, drove it once to O'Reilly for parts, then it broke down in the parking lot. By the time I reached that point I was just sick of it, I'd rebuilt most of the motor in the truck in my backyard just to find out that it needs a harness (PO was using it as a hunting truck, said he parked it in a 'creek' on his farm and left it all winter, the water line I found was just over the frame rail) and I could never bring myself to drop over a grand on a new harness for a truck I bought for 800 bucks, especially when I'm already in it another 500-600 in parts. I liked the Town Car, it was reliable transportation and it was cushy and quiet, but it was just...boring. My OBS has been a little touch and go, it's taking some work to undo all the hacky 'repairs' from previous owners, but I'm getting to the point where this one is giving me that same feeling I used to get from the Flareside.

Adding to what I've already read in here, I guess I've got a lesson to share as well for all my fellow young guys that have the itch for old iron.
ALWAYS BUY STOCK
It might be cheaper on paper to buy that lifted bro-dozer that already has Falken 35's on it, but you don't know what he (previous owner) did to make them fit. Also, research the hell out of any truck you're considering purchasing. I bet there's 5000 years worth of communal knowledge on this site about old Ford trucks (and that's just the heavily active posters), you may as well use it.