I started with a 110V 29 gallon harbor frieght 2hp oiled compressor. I would recommend that or something similar (oiled vs. oilless) to anyone who needed something to run an impact and air up tires, run nailers, etc. Anything shy of sand blasting, running sanders, die grinders, and HVLP paint guns anyway. I outgrew that compressor since I"m restoring a car and needed the output for die grinders, cutoff wheels, and paint guns and anything 110V simply couldn't keep up. That said it was a great compressor and worked well for many applications. I ended up giving that to my dad since his was old and the tank was rusting out and leaking.
When it came to upgrading there were basically three levels I was looking at that were on the radar. If you're going 60gallon+ and using 220V it seemed pointless to do single stage or one of the 3hp offerings in my opinion. They would be limiting in what I wanted to do and took up the same amount of space. For me spending the extra was worth it for at LEAST a somewhat honest 5hp compressor. At the lower level it was the Harbor Freight/Bel Aire/ and CP offerings which all seemed to be made at the same place. HF was the cheapest but probably the least warranty and support but all three (the same really) compressors had positive feedback.
Next up was the Quincy QT-54 which ran about 300-400 dollars more. on paper it had nearly the same specs as far as output of the "lower tier" 2 stage compressor or maybe marginally better. I did notice the shipping weight was substantially more, the entire thing was made in the USA, came with a BALDOR USA 5hp motor and a good warranty so in the end thats what I went with. I'm happy with my choice. I would have loved to go with a lower RPM pump that was quieter, and/or more output but the cost/reward diminished beyond this for the home hobbiest that I am.
Lastly and on the dream list would be an 80 gallon Champion or Quincy. Something with a slower pump RPM, magnetic starter, and 18+cfm. For this you're getting in the 2-3K and above range. My garage is very small and though 80gallon compressors don't take a lot more room, in my space it makes a difference and coupled with the cost difference was too much for me. In an ideal world I'd have the space and budget for this - and some people do. I think the quincy 60 gal will suit me for nearly my lifetime though.
For the big spenders with the room and budget there is always the 7.5hp and three phase type options, or refidgerated dryer screw type compressors but you're looking at major industrial duty and multiple tax brackets beyond me. A guy can dream though can't he? Even then its hard to justify that kind of capability for a household shop or 1 man operation no matter what your intentions are.
In short - Average DIYer 2hp oiled and nothing less.
If you have Autobody or restoration aspirations - no less than 60Gal 2 stage