Here is my experience with PSD and 315's.
I had an early 99 with a manual trans and went from the stock 265 to 315's. I saw a HUGE hit to my powerband and mileage. Empty my mileage went from 17ish to 14ish. Then I hooked my aprox 10K bumper pull TT to it. Oh my God! I couldn't even pull in O/D anymore except maybe on the downhill runs.
I ordered up a DP chip after hearing all the rave on thedieselstop.com I did the F5 switch with stock, 40T, 80T and econo. I ended up using the 80T as my daily driver setting and liked the power recovery. It more than made up for the tires. It rolled some mean smoke. The manual trans was nice for smoking ricers, just dump it in O/D at 30mph and pound the skinny pedal I could fog out the whole area
It was slippery as hell on snow and ice (too much torque), I went back to stock or sometimes 40T in the snow.
For towing I found I made WAY too much heat. I could easily hit 1400 sometimes 1500 on the pre-turbo pyro no matter what gear or RPM I ran. Most of the time on the hills I ended up just pulling with my stock program to try to keep heat in check. People from the board told me I had an intake leak (boost leak) I checked it found some small leaks, but saw no difference. I took it to two performance shops, one found the up-pipes slightly leaking, but no other leaks. I fixed those still no better. I finally put in a bigger intercooler (from a 6.0) that helped a little but still no better. I thought it must be the exhaust. I pulled the whole thing off except the downpipe, still no better.
The 80T setting would slip my OEM clutch if I made a hard shift fromO/D to 4th like when pulling a hill. I've heard pretty much all DP's tunes are hard on auto's, so start saving for an upgrade.
After all that then I noticed my turbo surging, where it never did that before. Since I had the early 99 I already had the "wicked wheel" everyone used to fix surge. So I was up a creek. I was set to do the 99 to 99.5 conversion and put a big a$$ turbo on it, but we found out a baby was on the way and wifey said no way an extend cab was going to work, so longer story short I now have a crew cab Dmax.
Everyone on the board said mine was just way too hot for some reason and they all claimed to tow the world on 80T. I know I couldn't. Maybe my truck was F'ed up
I don't know about re-gearing, in theory it should help, but no matter what trans gear (RPM) I ran I couldn't keep my heat in check. I read a few other posts that said the same thing after gearing to 4.30's and 4.56's.
I was ready to drop down to 285's, but the truck got traded first. I didn't really want 315's but I bought the rims from KSL and the guy made me such a good deal I figured the tires were pretty much free.
I think 285's are a good all around size. That's what I'll be putting on my Dmax when the stockers are done.
Good luck!