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Lol... I'm the youngest one in this thread and OBS are rough...
I just turned 30 today so I'm not old. lol mine is a SC 2wd and it rides like a tank but with a goose neck hooked up it rides like a dream. the end of this year I'll be getting a F150 with the 5.0 as my DD
I don't know if I really can add much, but off the top of my head, most SRW 350's will have a 3.73 rear end. PMR's can be fine. The rule of thumb used to be don't go over 400 hp with PMR's, but we've seen several tuners go well beyond that with no catastrophic results. I personally don't think there's a whole lot of difference between the E4OD and the 4R100 in terms of reliability.
I'd avoid the early 99 so at least you can get the cheaper bellowed up pipes for a permanent fix when the time comes. As for other upgrades, I'm sure you know about the electric fuel and 17 deg HPOP. You can stick a 4" downpipe on a SD without having to do any persuading on the cab. The IDM got tucked up under the fenderwell so it doesn't get wet anymore, but it's a pain to get to if you need to change it.
As for the downsides, transmission cooling sucks so adding a cooler is a must on the auto. The diode issue on the 01 has already been brought up, but these trucks are old enough now I'm not sure that's too big an issue anymore. Might be worth crawling under all of them and looking for a reman tag. The factory airbox absolutely sucks. When we were looking for a truck for my wife, I saw more trucks with dusted turbos or dusted engines than I could believe. Step one when looking at a super duty in my opinion should be to pull the lid off the air filter and inspect inside the intake tube. If there's even a hint of dirt in there, check the turbo wheel for dusting and start to think twice.
Other than that, I'd say it's pretty much like buying any other used 7.3. The good news is you can still come down here for 7.3 advice if everyone up there ignores you. I haven't figured that one out yet, but I've seen it too. I think part of it may be the guys in the SD section who know their stuff seem to be selective on which posts they participate in.
unit bearings are non serviceable when they go you replace them.
but they will give you plenty of warning. the passenger front on my 02 has been making noise for 30,000 miles , but only on a hard left turn under power.
the best of both worlds is a 03 7.3. but they are very hard to find because there were not that many made.
the only really important thing to look closely at are oil pan for rot, and cab corners, bed supports and wheel arches for rot