let me start out that 270 is nothing for the engine. when we pulled the head on my cousins truck at about that mileage the honing on the cyl walls looked brand new still. also these guys are right. my truck has a cam, fuel plate, and turbo mods, i has a 4in straight pipe exhaust, and boost and egt guages. this is my third dodge i had to learn things the hard way. this is the first truck that didnt have a big exhaust and or modified intake. ill tell you first hand i cant feel a bit of difference between them. the straight pipe on this truck is purely for sound not performance. first things first get a set of guages boost pyro and trans temp, then i personaly like to cut my own plates but to each their own. either buy or cut the plate. i can give you a rundown on how best to cut it or spend some time looking around on here and you'll figure it out. then put a boost elbow in the line to the wastegate so you can bump the pressure up, this is very easy to make, also adjust the afc spring and housing postion while doing the plate. i had a truck much like what your looking for that spun 33's on the dyno going into 4th gear, and i only spent about $12 in parts. these 12 valves can build big power with the stock parts, a handful of dollars, and the proper tunning. one thing to consider that i never did is a valet switch. this allows you to go pretty wild and by flipping a switch make it very very tame almost dead by comparision.
if i where to start over with an untouched truck my mods would be as follows. one: gauges, boost pyro trans. two: cut plate to a 100, slide plate and afc housing forward to some degree, and greatly lighten afc spring tension. three: install boost elbow and adjust for 32 to 35lbs of boost. four: straight pipe exhaust and install k&n or afe air filter(stock drop in not whole system). five: install valet switch. that combo will put you around 300 horse would be my guess, and when driven right will smoke out highways and roast tires and still drive very nice when desired. there are a lot of variables to this set up depending on what you want, and if this isnt wild enough then you can push it a little more but not much more without spending big money.
for the trans look into a converter, and a valve body for sure, help hold the trans together. without knowing the history of the truck my guess is you will probably be rebuilding that trans pretty soon. if thats the case go with a converter, valve body, and heavy duty rebuild kit. for more info look at suncoast or dtt.