Do I need an onboard compressor for 33-inch tires?

I run 33s on a daily-driven Tacoma and usually visit trails with friends. Is an onboard compressor worth the install, or should I stay with a portable unit?

For that use, a quality portable compressor is usually the better first step. It costs less, can serve a friend, and does not add another permanent electrical circuit. Onboard becomes compelling when you air up often, run lockers, or want integrated manifold control.

My concern is run time. After a day on the trail I may need to air up four tires from 17 psi to 35 psi. I do not want to wait forever or overheat the compressor.

Look at the compressor duty cycle at the pressure you actually use, not the advertised maximum CFM in isolation. Give it a break between tires if the manufacturer calls for it, and use a quality gauge at the tire rather than trusting the pump display.

A long hose and a good air chuck made my portable setup much more pleasant. I keep the compressor in a ventilated case with gloves, a tire plug kit, and a small pressure gauge.

That is a strong setup. The best compressor is the one you can access, power safely, and maintain. If you later add an onboard unit, keep the portable as a backup rather than selling it immediately.