oiled for me. year or 2 ago when shopping for one. i needed something that was light enough to be picked up and put in back of a vehicle and taken to various spots to be used, and also run off a 3000 watt generator.
granted i would of loved 30 to 100 gallon tank and a beefer 220 motor. that i could just leave in the shop.
for me the bigest tool was a "roof nailer" as far as amount of air and min pressure it needed to shot nails through shingles, tar paper, and plywood.
the only other tool that required more amount of air and a constant min pressure was an impact wrench. if memory serves.
when on the roof the one annoying thing was. after so many nails. i had to pop off the nailer, attach the air blower to hose. let air out, so compressor would kick back on. then wait for it to build pressure back up. before using it again. it took a few minuets, it was not all that long but annoying granted this is not a commercial thing. so waiting a few minutes most likely was a good thing for my body and gave me a chance to take a small break.
and for me, it was price tag that nailed me, but if i could of spent another 70 bucks, i could of upgraded to something that i could set the "pressure switch on" and would of not needed to use the "blower gun" to release pressure to kick on the air compressor. granted i could go get another pressure switch for air compressor i have now. and be able to pop the cap off and set things. but i honestly do not do shingle roofs that often ((years between each time)) but on the more commercial bigger units. awe. being able to set min / max pressure switch with just a little thumb dial. vs haivng to unplug and pop caps off and trial and error....would of been awesome.
to be honest, i think i would rather prefer any air compressor down on the ground. more so if you are doing shingles. by the time you got tar paper down, first few rows of shingles ya moving compressor around to do rest of shingles to peak. and with already having budles of shingles and rolls of tar paper up on roof to begin with. space can be at a premium. having the air compressor down on the ground. and not vibrating the roof. gave extra space, less cords / hoses on the roof. and perhaps a tad safer. ((i would hate to see air compressor fall down on someone let alone a car/truck / bush / etc... it would demolish that stuff if not put in a very expensive dent plus expensive repair on air compressor))
the one thing i hate about air hoses, more so long ones. is there is no easy way to roll them up easily. and ya end up fidgeting with the hose to put twists and like in it. as you roll it up. and due to that. i prefer say 25 feet vs 50 feet air hoses. ((makes for less of a mess as you coil them back up)) and you can add them end for end fairly easily and it only costs a couple bucks more for the ends.
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on another note. i have a old portable air tank. ya fill up with a tire inflater. and then ya take tank with you to were ever to fill up a tire or like down in the woods. i ended up buying a brass ball valve, a tee and some other fittings. so i could plug the tank in line with hose. coming from compressor. so i could have additional tank capacity. when i wanted to say turn compressor on and let it pump up over 15 minutes while i did something else then come back and blow out the garage floor or like.
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another thing. is upgrading the stinking small bolt. used to let water out of the bottom of the tanks. so the bottom of the tank does not rust out. be nice to have nice big thumb nut over the bolt head. i let water out during first use, and before i put it the compressor away. and that little 1/4" bolt just does not cut the cake.
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getting back on track. oil-less air compressors i have had. mainly been cheap little things, that might come with an air mattress. or an inflatable pool. perhaps a little 12volt cigarette lighter air pump. they are good for what they do. but once you get into blowing off mower decks and tractors to remove grass clipings and dust. along with using various air tools. oil-less air compressors seem to go down hill. to a point were oiled compressors are next. then jumped up to fan cooled or perhaps double staged compressors.