I started out with a 20 gallon, up-right, oiless, Crapsman, POS. It mostly did what I needed, LOUDLY, and often slowly, if I had it to do again, I would NOT buy that compressor. In fact, I'd just as soon never have an oiless compressor as my only/primary compressor again.
After the Crapsman burned up (common issue on the model I had) I bought a used Speedaire (Grainger house brand) 20 gallon, horizontal, oiled, single stage, twin cylinder, compressor that had sat in front of a local pawn shop for months. It was neglected and in disrepair. It had 1/4" of dirt on top of the pistons from being ran without a filter. It wouldn't pressurize past 40 PSI at the pawn shop, and I talked them into letting it go for $30. I bought a ring kit from Grainger, spent a little time with a hone, cleaned everything, put a new unloader valve on it, used the pressure switch from the dead Crapsman, and had a decent compressor for less than $100.
I still have the Speedaire, but it was limited in capacity, and a few months after rebuilding it, it developed a big issue, either I screwed something up, I tend to do that, or got a bad part when I rebuilt it, I found out a several years later, when I finally investigated, that one of the new rings I put in it was broken, it caused oil blow-by worse than anything I have ever seen, and would quickly fill the water/oil trap on my regulator. This made the compressor fairly useless for painting, or much else for that matter, and I eventually got frustrated to the point that I said screw it I'm getting a new compressor, and I'm getting a REAL compressor.
I had a $500 budget, and went on the hunt for a NEW, large capacity (50+ gallons), air compressor. After comparing all of the options on the market at the time I decided on the Kobalt 60 gallon compressor from Lowe's. It was near the top of my budget, but inched out it's competition in most categories, 155 PSI where most are 150 or less, a couple more CFM @ 90 PSI than most others, and with a Lowe's card you got 0% interest for 6 months. I still feel that for a single stage, home shop use compressor, for the price the Kobalt is the one to get. Only downside is it's 220V, and it takes up some floor space. Kobalt 3.7-HP 60-Gallon 155-PSI Air Compressor
So as the evolution of my compressor ownership continued, I moved to a 1 car garage townhouse in Ohio, the Kobalt got moved to my parent's barn, and I took the Speedaire and a Porter Cable pancake compressor with me. I used that pancake compressor A LOT, it's oiless, so LOUD, tiny capacity, so it cycles often, near constant when using the impact a lot, but it worked in a pinch.
I finally got to the end of my rope with the pancake, and decided to tare the Speedaire apart again, discovered the broken piston ring, put new rings on it again, and started using it again.
We eventually left OH, and have been back home for about 6 months now. My Kobalt is still in dad's barn, I still have the Speedaire and the pancake as my go to compressors.
I needed to add air to my tires last week, the Speedaire was empty, so to save time I grabbed the Porter Cable pancake.
If we weren't in a rental and/or the breaker box wasn't outside on the other end of the house, I'd have 220V wired in the garage, and my Kobalt would be in my garage closet.
Cliff's Notes: Don't buy an oiless, buy the largest capacity, highest CFM you can afford/have room for, I like the Kobalt 60 gallon compressor from Lowe's.