I'm not sure you really NEED to do a lot of mods to pull a 5K trailer. My 97 only has a new exhaust, 3k gov springs, exhaust manifold, and new air cleaner and I just got done pulling a 4 to 4. 5K trailer between Colo Spgs and Pheonix(gears are 3. 5s?). Maintained 70+ the whole way except on Raton Pass and up the hill to Flagstaff from Pheonix (got down to 65 there). EGTs maxed at less then 1. 2K.
Matt pretty well nailed the sequence in his reply but I'd suggest a transmission temp gauge and EGT first if you only go with two gauges. For what it is worth, it is really as easy to put in all three gauges as once as two and the overall cost won't be tremendously more.
As you have probably read the trannys in the 2nd gen are pretty well known for being a problem. If the transmission is still in good shape, you may want to install a quality torque converter and possibly a quality transmission valve body, right away(if the tranmission is already suspect then I probably wouldn't put either in it). From what I understand, many of the transmission failures are caused by the stock torque converters self destructing or leaking valve bodies and taking out the transmission so putting in a quality torque converter and valve body might extend the life the transmission for quite a while.
Regarding the supply/return lines, if you have problems with the truck, those lines can be right in the middle of alot of the symptoms. If they aren't good it appears they can really lead you astray and cause you to replace parts that aren't bad. If you get into starting, smoking, or fuel economy problems they are something that should be looked at.
Something else to consider is to install a summit wiring harness. That will help protect the headlight switch and provided better lighting at minimal cost($50).
You might also want to look at how much the truck wanders if any. If it does then look at a DSS or 3rd Gen trackbar mod.
If he is in the truck a lot, then you might want to look at putting belsteins shocks on it also.
A spray in bed liner is awful nice also.
I really didn't seem much performance improvement after installing a 4in exhaust so I wouldn't make that really high on the list of mods. If I did it again it would be well after the gauges, wiring harness, and transmission work.