I suppose this is the best place to ask this, as I feel the main issue with this will be the turbo aspect of it. I have a plan for a fun/work truck and feel like it will work out, but would love some feedback in case I'm missing something obvious or it is just plain a terrible idea to attempt.

As some backstory, I had a Subaru Legacy GT as my fun car, but rarely put on 1k miles a year and it just didn't make sense to have anymore for what insurance cost me. Well two years later and I'm really missing the boost, but I also need a truck bed for hauling random crap around and pulling trailers. Per my wife I already have too many vehicles, so getting a truck for truck stuff and a car for fun isn't allowed unless I sell my Jeep, which isn't something I can part with. As far as I can tell that leaves me with one option, get a fun truck.

So the plan is take a 96-98 Silverado/Sierra extended cab (personally my favorite body/interior style, and huge bonus that they are cheap), drop in a 4.8 from the scrapyard and boost it to ~600 HP. Living in the country I'll need 4wd, so the first issue is how well will that hold up and if not well are there reasonably priced aftermarket options to beef it up? Not planning on romping around with 4wd, but it is still going to wear on the transfer case in 2wd right? Next is if I will run into issues hauling trailers around with the truck, nothing crazy, say 5k pounds or so.

As for a rough idea on what I'm getting myself into cost wise, am I missing anything major?
$250 Junkyard 4.8
$500 New cam and springs
$1200 Demah 78mm Turbo kit
$750 Headers and exhaust
$500 Injectors
$1300 Holley Terminator
$500 Misc Stuff
$500 Secondary Misc Stuff

Sorry if I'm asking some obvious things here, I just started a bit of research into this and now trying to figure out exactly what I need to focus on researching. Thanks in advance.

 

don't forget your transmission... because yours surely won't forget the power bump.
if you want to plan on a 4L80, the 32spline t-cases from a HD truck should swap in pretty easy & be beefier (make sure it has a pump rub kit if it's a 261).

 

My stock 4L80E lasted 3 months behind my turbo LQ4 at 9psi before it started making noise. Was completely fine before that for 305,000 miles. Jake's stage 4 rebuild and a Circle D convertor, I have $2700 in the trans alone and my truck came with a 4L80E (no conversion stuff needed). I rebuilt the trans because of the mileage, so keep that in mind if you are looking for a 25 year old truck. I would say with the trans upgrade, I probably have close to $10k in turbo stuff and beefing up my truck which wasn't much because it's a 3/4 ton drivetrain. I bought a Trick Turbo kit because I didn't want my truck down for a long time while I figured out all the bends and such. So you can save a bit building your own if you have the time. I did save a lot of cash welding up my own stainless mandrel bend exhaust, which on my 1500HD was easy. Again mine has a ton of miles, so I didn't want to put 305,000 parts back in, like the convertor, so that runs up the price. Something to think about on an old truck.

 

The 4wd stuff is pretty decent, but that generation (GMT400) lends itself to a 9.25 front end swap super easily

T case in 2wd is straight thru, no concerns. Personally I would do a 32 spline 241 from behind a manual or 4L80 truck. Lots of flavors to choose from

The 4.8 is a great motor, but down on torque. You may wish to have more torque especially with the steep 4L80 1st gear

Towing with boost is easy; if you're smart and have a good tuner. The best hard parts you can throw at it for towing is cooling the coolant and oil. Leave the mech fan if you plan to tow A LOT, otherwise e fans will get ya where you need to go.
Swap harness is easy to come by for ~$500 on the high end if you dont want to wire it yourself. Absolutely do a 0411 and save the cost. No need for a $1300 ECU on a 600hp build; imo. Remember tho that your timing will be lower for a tow safe tune, so you may want to invest in HPTuners so you can flash your "Friday night fun" file and your "tow the broken junk home without pushing water" file