My 6.5 has most of the mods joez truck did. I have done an exhaust (3" downpipe, Duramax 3.5" tailpipe, no muffler), Heath Diesel programming (Heath, Westers, and Kennedy all seem to have about the same power results), Turbo-Master (eliminates vacuum wastegate, manual adjustable boost control), intercooler, and a few minor tweaks such as advancing the IP for a few more HP. My truck is no rocket, but it does well. I have towed all over the country (and into Canada) without major problems (I bought it in 2001 with 86,000 on it, now over 160,000 w/original engine/trans). Towing my Blazer, I gross about 17,000 if I carry a lot of spare tools/parts. With my travel trailer, I would gross about 14,500 by my estimate. When I moved from CO to VA, I was loaded by my estimate to around 19,000 gross and did just fine.
One of my only complaints/issues would be somewhat uncontrollable trans temps with stock cooling. Definitely an issue towing through CO, not so much back here on the east coast. I got my transmission hot as crap a few times pulling through the Rockies. Biggest problem is that you can't keep up enough momentum to keep the converter locked, which keeps the transmission cooler.
I would say the load you are looking to pull is doable with a 6.5 with similar mods to mine, just don't expect to keep up with a Cummins or any other "modern" turbo diesel truck. Here would be my list of pro's/con's:
Pros-
-cheap (relative to similar trucks as said above)
-quiet comfortable interior (at least with front buckets)
-easy and cheap to improve (both mechanical and interior/exterior)
-strong dependable drivetrain
Cons-
-not as many creature comforts as the newer trucks (at least the 95-up, I hate the 94-back interior)
-block cracking issues on 97.5-99 (although I have one of the "bad" blocks with no issues)
-high CR limits boost level
-lack of rear opening doors on EC trucks (available on half tons 96-up)
-transmission cooling/converter lock up control (although fixable- and easier on the OBD1 truck- or find a 5 speed truck)
-injectors only "good" for 100,000 miles or so (but this could be a pro- new injectors cost less for a set then 1 injector for a Duramax), ine are original but fuel mileage has dropped a bit over time.
That is all I can think of now. If you have any specific questions, fire away. I will check back here. BTW, the best resource on the internet for this generation of GM diesels would be the 6.5 forum on dieselplace.com. Large following of regulars over there and very dedicated to keep the 6.5 alive and strong, and they are easy on the noobs.
BTW, if you have 6.5 pulling a load and it smokes heavily all the time- something is wrong, and most likely the vacuum wastegate system. So many people have that issue and just blame the lack of power on it being a POS 6.5, instead of getting it fixed correctly.
Edit- thought of a few more things.