Not sure when or if I need to get a custom chip for my car.

It's an original '89 305 tpi automatic car and still has the original chip.

Now it has headers, 350 injectors, higher fuel pressure, pulleys, a five speed, and 3.42 gears (instead of 2.98s or whatever they were. Also thinking about changing to a stock LT1 cam. Might do some basic intake porting this fall as well.

At what point do I need a chip?

 

You needed a chip when you changed the injectors. I am assuming that you are running 22lbs injectors, correct? Your car must be running quite rich with the bigger injectors and higher fuel pressure.
Any cam upgrade is going to require tuning (chip burning). Also an LT1 cam is not much bigger than an L98 cam.

 

Yep 22# Bosch IIIs. Seems to be running great, except idle is rough and the rpm often surges at idle. I disconnected the IAC which made it a little better.

I know the stock LT1 cam is about like an L89, but I'm dealing with an automatic 305 cam now, which is something like .380 lift. Thought the LT1 stick would give my 305 a little more legs.

who's a good chip provider.