I used a cheap single stage compressor for years, and had no problems when the required pressure was below 90 psi. The thing worked hard, and didn't sound all that great, but it did the job for over 25 years. It's major limitation was the maximum pressure it could put out.
When airing up the tires on the trucks or motorhome it just wasn't up to the job. The maximum pressure the pump would put out was 125 psi. While it was high enough to do most of the vehicles it struggled for those that needed 110 psi to 125 psi. If the tire(s) needed to be topped off (especially in cold weather) it took forever. Since the differential between what the compressor could put out and the pressure needed was minimal the tank had to be charged to the maximum.
Once the pressure was near the differential point air flow was reduced to a minimum. The tank pressure had to go down to 80 psi (highest the switch could be set for) before the compressor would restart. I had to constantly bleed off air to get it down to the start pressure. Then I had to wait for the tank to build to full pressure before I could continue to fill the tires.
One downside of a single stage compressor is no pressure relief (unloader) valve between the head and the tank. The compressor has to start at whatever pressure is in the tank. It's difficult for the motor to start the pump when pressures are above 80 psi, so that's generally the highest setting available to restart it.
On a 2 stage pump the unloader eliminates that problem allowing the pump to be started with no head pressure. Thus the minimum kick in pressure can be set higher.
Here's a tutorial from Quincy as when to best use single and 2 stage compressors
Single Stage vs. Two Stage Air Compressors | Quincy Compressor
As for automatic tank drains there are several on the market ranging in price from $65.00 to over $200.00. I have no experience with any of them so I can't comment on their quality or reliability