tbi can be rewired for tpi, I would read up on that process, lots of info on thirdgen.org.
MAF is ok, but the MAF itself is very costly compared to MAP if you have to replace it. MAP is not as "adaptive" to engine mods as MAP, but if you end up with '89+ TPI(think thats right) you will have to deal with the VATS issue in the ECM. Then you start getting into custom PROM burning, etc., which also isn't bad. TPI can really be tuned to "perfection", burning your own chips is the only way to do it though. Don't HAVE to, I'm running an '87 305 ECM with my setup right now, until the chip burning stuff shows up, but it doesn't run as well as it can.
Stay away from '85 TPI at all costs, especially since the intake bolt pattern will be wrong for you.
There is a lot to the swap, but since you are already TBI, I *personally* would run the stock harness, especially if you know it works now. No matter how you slice it, there is going to be a huge learning curve, and there should be. Once you understand what does what and goes where, you won't be so intimidated.
Check out thirdgen.org's classifieds for setups. I got mine for about $500, but I'm not sure if the guy is still selling them or not. Complete take-offs from cars.
Get a service AND wiring manual for the year injection setup you end up with, and you'll need one for the truck too, at least I did. Maybe not if the tbi->tpi re-pin of the harness is straightforward, but I needed to know how the stock truck fuse panel was wired for my '86.
If anyone tells you you don't need the manual(s), they are moronic. You can spend 100's of dollars throwing money at injection parts in a heartbeat, where a manual's troubleshooting flowcharts will save you a ton of time and money in the long run alone. Besides the fact, once you have a manual, you will spend hours reading it, as they are that informative, and make so much sense.