Why oil-less? I was pretty well convinced (based on previous research) that I should avoid the oil-less units.
You mentioned wanting to get into spraying finishes at some point in the future. Conventional (oil lubricated) compressors sometimes deposit a small amount of oil inside the air lines, which can create major problems in a spray finish.
Additionally, over time you may end up with a small amount of oil inside your air lines, so even if you used an oil-less compressor in the future for spraying, you would also need to use clean air lines as well.
Granted there are oil separators available, but it's best to avoid the problem if possible. One of the best spray finishes is from an HVLP setup with a conventional gun that converts high pressure into high volume at the gun. These models tend to flow a lot of air, so if there are oil deposits inside the line the higher air flow is more inclined to pick up the oil residue.
Oil less compressors have come a long way, and are a good choice for light duty use (which is basically the applications that you listed).
For heavier duty use,
yes an oil lubricated compressor is a better way to go, and if you are purchasing the "compressor of a lifetime" oil lube would probably be a better choice. Decisions for oil lube included splash versus pressure lubrication (the latter being better). Addtionally, you can decide between alumimun or cast-iron material for the compressor and head (with CI being the more durable choice).
What type of budget do you have? Northern Tool has an 18 cfm IR oil lube for a little under $900.00, and a 10.3 cfm version for $630.00, both 60 gallon tanks.
Sears has a Craftsman Professional model, 60 gallon oil-free 9 cfm for $617.00. Sears also has an 80 gallon, 2-stage cast iron pump oil lube model with 13 cfm for $950.00. Other than a low CFM, that's a lot of compressor for the money.
Since we're talking more serious compressors, one major advantage of a two stage model is that the tank pressure is usually 175 psi - about 40 psi greater than a single stage model. Compressed air volume is not linear - the higher the PSI the greater the volume of air that is compressed into the tank.
Lots to mull over, eh?!