Chevrolet Camaro 1967-2002 - Rebuild or replace 99 Z28 rebuilt title

Just looking for some opinions/thoughts. My car is a 99 Z with, as of today, 168k on the clock. I've had it for two years now, and I love it... its taken everything I have thrown at it and then some. I bought it for 2k. Previous owner wrecked it on the ps front, and had it fixed, although they did a crappy job of it. Since I have had it, I fixed his f-ups, save for the paint job... which I think trained monkeys could have done a better one. Well, long story short, I'm about be be getting deployed again, and I was thinking of dropping in a new motor, have my brother rebuild the tranny (4l60e), and a fresh coat of paint... everything else on the car is in good shape... my question is, what are your thoughts on doing this, or just buying another one with lower miles and a clean title? I have no intention of ever being camaro-less, so the resale isn't the issue. Plus, this particular car has a bit of sentimental value, as I got it shortly after my best friend, and camaro/drag racing freak, passed away. And I have quite a bit of trophies on my shelf from racing this car as well. I'm going crazy wrestling with this in my head!!!!

P.S. I want to keep things cheap as well...

What's wrong with the motor and trans it has now? If there's nothing wrong with then just put the money into the paint.

She's starting to show her age. Valve guides seepin I think (puff of smoke on takeoff). Plus a pretty bad leak from the top of the engine i cant find... and the tranny, again, just the age, could prob use freshening. I am getting out of the service after this deployment, and would just feel a lil bit more comfortable having the major money/time stuff done before i make the job transition... last thing i need is her breaking down while im jobless... i figure while i have the money to do it, get it done so i don't have the issue at a bad time. Tranny wouldnt get replaced, just refreshed... and as far as the engine, i have seen that rebuilding it would cost damn near as much as a new short block.

U answered ur own question with the sentimental value ....if u like the car rebuild her...make it ur own...