Generally TJ's are pretty easy to work on.
And these days with the net & internet forums - generally helps is pretty close at hand.
Personally I prefer to do all my own work because 1. I save money, 2. If I stuff up there's only one person to blame

.....But IMHO the more time you spend spinning your own spanners the more you'll learn how the vehicle works and have more $$ for mods.
Anyhow let me finally throw out my 2cents
Firstly sadly $5k can be chewed VERY quickly on a TJ. Eg Regearing & lockers - boom - you've just blown about $4k (depending on the locker choice). And sadly this is one of the biggest weaknesses of the TJ - the stock gearing SUX.
So the very first things you need to get is a plan, IMHO also scour the Trading Post and places Like AusJeep or Here for parts for sale - to help keep the $$$ down.
Infact just about everything hindges around the tyre size. For a Daily Driver I'd suggest 33x10.5 is a good size to aim for. Means you cn retain you current rims and flares. but also is better onroad.
So targetting 33x10.5's:
1. I'd go 4.56 diff ratios (but if you have an Atuo I'd prob go 4.1)
Dual lockers of your choice Detroits being cheaper, ARB more $$ but better onroad.....
This alone will make THE biggest difference in your offroad ability - but should also allow you to move to bigger say 35's in the future is you so decide.
2. Ok you've blown most of yor budget - so now I'd suggest a 2.5" Lift & 1" BL with 1"mml. This will empty out just about the rest of your budget but these items can be installed DIY. You may need to drop the bump stops a little bit more to prevent tyre rub - but this combo IMHO is the best fit and would work great offroad.
3. Front Swaybar discos are also a HIGHLY recommend item.
How's that for starters??