Similar situation.
I'm in a similar situation. With the exception that I have 145k miles and my TC is shuddering worse and worse.
Transmission:
Bill K. at DTT (1-800-922-7782) or his son Shanti (?) will probably tell you to turn up the line pressure and drive it till the transmission is totally shot. They will also probably tell you that it would be a waste (both time and money) to put a new TC and VB into a transmission with your miles. The stock trans does not have strong enough seals to handle the higher pressures of a high performance VB. You want a high performance VB! You want a stronger torque converter! Also, if you do put in new TC/VB in your old transmission and a gear/clutch desintegrates, it will shoot crap throughout your new VB, cooler, and TC - which is very hard to flush adequately (almost better to send it back to them to service).
If you're going to increase your hp much, a stock transmission or local rebuild will probably not last very well. You'll pay a little more than your local shop (+/- $500), but you'll get a MUCH MUCH stronger trans that WILL hold up.
You can wait till it dies (another 1,2,3,... years later) and then upgrade or replace it now while you still have some good years left on your truck and start enjoying it. For the money, I wish I could limp it out a few more years, but can't. The TC is shot.
Bill told me that I'd need a minimum of 230 HP to properly run one of hisTC's if I was going to tow much. Otherwise it would stall-out when rolling off the line. I'm stock 160 hp now. In order to boost my HP, I got a set of DD Stage 3 Injectors - $400 (usually around $560). Stage 2's would have been sufficient. I also got a new set of 191 Delivery Valves - $230 (that are needed to support the injectors. Also to be installed with transmission). I installed a 4" exhaust to help reduce EGT temps - $450 (which will undoubtedly be created with the larger injectors. I got a set of gauges (EGT, Trans, Boost) - $200 (to monitor temps. Also to be installed with transmission). On a whimm, I also ordered a 3K Governor Spring Kit, Boost Elbow, and #4 Plate (from Piers) - $350.
If I DIDN'T have to repalce my transmission, I'd get a Torque Plate and 3k Gov. Spring Kit and run them till the transmission died. I'd also turn up the VB line pressure to help the transmission last as long as possible.
Then, once my transmission was dead, I'd repalce it with a high performance one like DTT, ATS, or BD. These trannys are MUCH better than anything you could have built for you locally. These companies KNOW the torque our engines put out and have made high perf trannies their passion. Then, if and only if, the new transmission requires more HP, start asking ?'s about this upgrade at that time. Note: You may end up replacing your plate again with yet another one depending on how much hp you added since your last plate. Plates can be an iffy thing and may need to be changed of yu continue to tinker. I feel a gov spring kit is a sure thing - more than likely, you won't be changing it later no matter what new mods you make. Develop a good road map (target hp, torque, drivability, $ willing to spend, etc) and stick to it. this will minimize your chances of duplicating and re-re-re-modifying later.
Bottom line - it's your money. Spend it when and how you want. I'm new to a lot of this stuff myself and am no expert, but I've spent countless hours here asking the same ?'s you are. A lot of the recommendations you'll get are personal preferences and your decision will be a preference to. Get as much advise as you can. Call as many Pro Shops as you can - Piers, TST, BD, DTT, Auto Wurks Diesel, etc. etc. ). Decide what makes sense to you. Then when everything get's real fuzzy and confusing, and your head's about to burst, find a TDR member who you trust and start working with them to help you develop your road map or make your next move. By then you'll know a lot more about how things work and you'll be more confident in the direction that you want to go.
The only hard and fast rule you must follow is don't add fuel without FIRST adding gauges. I see you've already noted this. The rest is up to you.
Good Luck!
- Bruce