Brands vary, you often get what you pay for.
Look at off-roading sites and go with a well rated suggestion from that area as they use compressors often in that hobby.
Off-roading you often let air out then need to replace to drive to go home using the vehicle.

Hose length...
What ever your truck & trailer length is when hitched together is a minimum with extra so you can reach easily.
They make coiling airhose similar to water hose...again quality matters for best PSI given if you need to air up to high rates you don't want to be stuck an hour with a struggling compressor....
🐴....

 

Second thought....
Consider a under hood mounted compressor.
Runs when truck runs & turns on/off by a toggle switch.
Hubby had on a truck when we were dating & indeed went off-roading on the beach and mud-flats weekly x many nights.
We (he) aired down to drive very soft deep sand, then aired up to head for home not taking wheel off the rim....
Others be sitting forever doing the same, he did 4 tires in minutes and we be headed homeward.
Only downside is if you use multiple tow vehicles it's not portable.
🐴...

 

Stroke of genius

 

this is the one i keep on hand and has worked great for me. My fiance is a handyman so we have several batteries charging at any given time and I just grab one before i head out. Amazon.com: RYOBI 18V ONE+ Dual Function Battery Powered INFLATOR/DEFLATOR. (Tool only). : Tools & Home Improvement

 

I have a Viair and they are a good brand that works well. Just be aware that most cigarette lighter style powered one’s may not have a long enough cord to reach back to the trailer tires from the TV. I use an adapter for the 7 pin trailer plug and still have to back to each side.

 

We picked up one of these for each of our vehicles when they were on sale at Christmas time. Hubby has used them on car, truck, and trailer tires. He loves them. I personally haven’t had the need to use one yet.

18V ONE+ High Pressure Inflator with Digital Gauge

RYOBI introduces the 18V ONE+ Cordless High Pressure Inflator with Digital Gauge (Tool Only). The Cordless Power Inflator is the perfect tool for tires ...

www.ryobitools.com