1988 Chevrolet Silverado Cutting out / flooding possibly

Check fuel pressure with a gauge, autoparts rent it. If tbi should be 9-13 psi. Also check under tbi unit for a blown gasket usually in the rear.

I doubt it you'll probably have to get an adapter. Of course your could always LOOK it would be a Schrader valve

Scan for codes and check vacuum at manifold if 15" or below suspect clogged converter then check compression

Also do your basic ignition checkes like adist cap wires plugs etc.

One other thing I forgot as it's been so long for me to even see one of these earlier model truck is to check the vacuum line going to map sensor. If it's soft replace it as it may be sucking together an d not letting the map work right. Also make sure the wires on top of tbi unit are making good contact as those could cause some of your problem as well. Other than that I'd really have to see this to fix it. Also if you can short the cylinders out and you find one that is missing then pull the valve cover off to see if it's a valve problem or bad cam

I would inspect and test the igntion system (spark) first before anything else because it seems to be running just not well so I wouldn't suspect fuel at this time.
Pull spark plug out and make sure they're not worn or black & wet looking. Next check the resistance of each spark plug wire. For every foot of wire should be 1000ohms or 1.0kohms. Wiggle the spark plug wire while testing to check for any breaks in the wire. Next is the distributor cap and rotor. Inspect for any carbon trails where spark is leak or shorting to ground bypassing the spark plug.
These parts are fairly inexpensive to replace on GM products and are considered maintenance items.
It looks like you have a scanner to read the data the vehicle's computer is seeing. Can you provide the short term and long term fuel trims (abbv. LTFT & STFT). If not then the oxygen voltages (both driver side and pass side oxygen sensors if equipped with more than two).
Hope this helps and let me know what you find before you go spend money on tools.

Great. Sounds good. Talk to you soon.

Did you get a new rotor for the distributor also?
Have you checked timing?
When you asked for first question you provided some data from some sort of scan tool. Do you have access to the Long and Short term fuel trims (abbreviated LTFT & STFT) on that data list? This will help indicate whether or not there is a disruption in the air fuel mixture assuming the oxygen sensors are reading correctly.
If the timing is correct the next items are probably sensor related.

When you can explain what is happening on a cold start up or the issue your having on start up?