i'm in the uk, so things may be a bit different (we're on 230 volts for a start)
but i got a compressor about 10 years ago,
i looked at the cfm requirments of all the tools i wanted to use, wanted to use a spot blast gun, so needed over 7cfm for that, and the compressor i chose has i think 9.5 cfm rating... but beware, that the cfm rating on compressors is like the peak watt rating on speakers and amps, it's the absolute max recorded during destructive testing in lab conditions.
there is another rating that shows the real world air volume delivery, cant recall what it is tho, but my compressor is just over the 7 cfm in real terms that i needed.
i got a 50 litre tank, direct drive single piston unit, think it has a 2.5 or 3 hp motor, not sure of it's power consumption, we can pull 13 amps from a normal socket over here (that's at 230 volts remember, and thus is just under 3 KW
it as set to 120 psi, but i was able to adjust it to run at 150 psi on the cut out switch, the tank is certified to something like 250psi, and it's a common thing to bump the pressure up a bit on these compressors, the instruction manual showed how to adjust the pressure switch and what the safe settings were,
i needed the higher pressure to run my air greas gun, which i use to grease the UJ's on my motorhomes propshaft, at 120 psi it didnt have enough pressure to get grease in them all the time, at 150 it always gets the grease in em,
my biggest regret.... going for direct drive, noisey, due to the motor having to run so fast, i really wish i'd spent the extra and got a belt drive compressor, but then i'd have wanted a twin piston compressor head, an after cooler, 100 litre tank and so on, i'd prolly talk my self into getting a 3 phase model so i could get 50 cfm and 200 psi up in 10 seconds if i didnt keep my self in the reality zone

But honnestly, if you plan to use the compressor a lot, try to get a belt drive one, much quieter, less stressfull on the motor, lower power draw etc,
and as others have said, avoid the oil less ones, the oiless ones over here at least are piston compressor heads (the diaphram ones are more for air brushes, nowt serious can be run from a diaphram compressor)
just the oiless compressors have teflon coated cylinder walls and teflon block bearings, ok for occasional light diy use, but run them too long and they wear out very fast, and they are then a throw away item,
oiled compressor heads, you just need to check the oil lever every so often, think i check mine every year, change the oil every 3 or 4 years, and if you wear a bearing out, you can get replacements easily from any beariung supplier.
My compressor has a built in regulator, but also has an unregulated take off point in the form of a large allen screw in the centre of on end of the tank, i've not used that yet, but plan to get an external high volume regulator one day, and feed it from the centre take off like they do in pro instlations.
other maintinance... drain the water from the tank often, all compressors buil up water in the tanks, moist air is drawn in, and gets trapped in the tank, some better compressors have auto drain valves that open for a second every time the compressor shuts off.
i believe you can also buy an auto drain valve kit from your big diy stores in the us to etro fit, i'd highly recomend one, and wish i could get one cheaply and easily over here.
i have my compressor located in a store room at the end of my garage, i then ran some nylon air pipe from it, and down the length of the garage, i have a tee halfway along with a drop to a standard airline quick disconnect, and the rest of the lines run terminates at the front of the garage in a 25 meter long self retracting hose.
tools i run... spray gun, touch up gun, grease gun, caulking gun (with an adjustable regulator on the gun, otherwise you empty a cartridge in 2 seconds

spot blasting gun, blow gun, drill, die grinder, cut off wheel, air chisel, sheet metal nibbler, shultz gun (under seal sprayer thingy) parafin/gunk sprayer gun, 1/2" impact gun, 1/2" ratchet driver, (could do with a 3/4" impact gun for half the nuts on the motorhome) and of course a tyre inflator gun (one for commercial vehicles, with the long stem dual ended tyre valve fitting to inflate dual rear wheels, and able to inflate to around 80 psi and still be accurate)