Doggystyle

First of all i love my car. Its a 99 and its been really good to me. I did little stuff like airbox hack and rear muffler delete and poly sway bushings. But i'm hesitant to dump and real money into it because i'm not sure it its worth it. I know in the end i'm gonna want my everyday driver to run somewhere in the 13's and trap maybe 105. I miss driving my trans am but its a POS compared to my gold buddah. The car i really want to get is a 2004 xjr and they sell for about 18 right now and my ls is worth half that.
I dont want to make my car less reliable but can we safely and affordably boost these engines? I've seen some complicated and expensive looking FI setups here and i dont want anything like that. I was thinking of replacing the middle resonator with a STS style turbo and maybe a e-cutout right after. This way seems like it would be alot easier than trying to fit it under the hood and i'm sure it would be a bunch cheaper because its alot less plumbing than running a turbo behind your radiator.
Can the engine handle 6lbs of boost and still be reliable? If i have to mod the engine internally or replace my rings down the road then its not gonna be worth it for me and i may as well save up for the XJR. Also what about eh transmission? Like i said i'm not wanting a 500hp race car but something that is reliable and can trap at about 105.
FYI i would have totally bought a GS400 but i sat in one and bumped my head. I'm 6'5 and i needed the extra space the LS offered. When i drive my wife's 04 prius, the mirror is at face level. When cruise my LT1 trans am i'm at a stupid reclined angle and the bolsters dig into my lats. There are not alot of fast cars that are tall man/bodybuilder friendly.
I'm not interested in a Used M5 or CTS-V because clutch jobs are expensive and i like to eat, talk and smoke doobies when i drive.
So anyhow let me know your opinion. Is it possible to affordably boost my car and make it comparable to an XJR? I figure new struts and springs are gonna set me back 500-600. All the parts for the turbo install would be about 800-1200. I would appreciate someone smarter than myself to chime in and tell me what this is really gonna cost me. Also if i'm running intake pipe half the length of the car would i even need an intercooler?