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If you go with a power adder, one area you want to pay close attention to is the transmission, especially an AOD; because heat will kill a transmission. A larger transmission cooler and a shift kit will definately help. As for your 8.8, 3.55 gears work well with an overdrive transmission, however, I'd suggest looking into a good limited slip locker Like an Eaton because traction will be an issue with a power adder and a non locking differential.
Running an intercooler is a good idea if you plan on an 8psi application or higher, just make sure your fuel system is able to support the added power your motor will make with a supercharger. The speed density ECU's cannot calculate anything above 99.6 engine load (or .996 volumetric efficiency) which makes fuel pressure extremely critical.
What power level are you after and how much money are you looking to spend.
Im thinking around 300 to 350 horses with as much torque in the low to mid range as i can get. 350 to 400 ftlbs or so cus after all this is in a truck.
As far as price, i dont wanna go way over the top but am ready to spend quite a bit.
Im also going to have to disagree with your trans being ok with these upgrades. I had a 90 F150 with a stock 302, and i could not keep an aod in it. Burned up 2 different trans, and had seperate moderate things go wrong 6 different times. Ended up putting in a C6 because i could not stand the aod any more.
With a power adder, I'd also suggest installing a shift kit, traction bars, and a limited slip differential at the minimum. Most all SC kits are made to run without tuning; they use a boost timing retard and an FMU to control fuel and timing advance under boost. Aftermarket tuning would be a better option; there are still a couple of tuners that can work with speed density and boost. Or, you can buy tuning software and tune it yourself. Either way, I'd stongly recommend a installing a cab mounted FP gauge and a wideband O2 to monitor fuel pressure and air/fuel ratios.
You can fabricate your own ductwork to utilize an air to air intercooler, or go with a water/meth injection which also works well for air charge cooling.
The question was will the AOD handle the motor with cam and exhaust... no blower, and I think it will as long as it's healthy to begin with, is properly calibrated(TV cable), and has a shift kit installed. It will need a complete overhaul/upgrade to handle the motor with a blower added though.
Unless your transmission builder can guarantee you for at least six months, within that time frame the bugs (if any) will work themselves into a noticeable problem. For the record i put nearly $3000 into an aod (parts & labor, i bought the parts) and tuned the tv with 5 different known accurate pressure guages, followed so many different sets of instructions that all said the same thing, didnt help. He even tuned it several times to "make sure I did it right". It couldve been the builder, but ive seen his trannys do really well for 4 years. I blew 4 up in 5 months, with 475 whp and 430 ft lbs. Of course the dummy didnt get a new t.c. so the last three were probabally blown because of the first failures fragments being stored in the t.c. I have 3 perma cool tranny coolers (1 has a 10" fan) that were all brand new when he started and they work great now, after a good flush. I ended up taking the guy to court because he would'nt refund me, got my money back and then bought an ATI built C6.
I can't model the intakes in DesktopDyno because there is no flow data available for them, but it's safe to say it will produce a broader powerband than the stock 5.0 truck intake. With GT40p heads the motor will produce more TQ and HP because the heads flow better and because the smaller combustion chambers raise compression ratio. Overall I'd be surprised if the actual motor didn't surpass this prediction.