Older model Shoebox Max 4500 psi model

Lubing is not hard. Just put a few drops of silicone oil on the piston rods every hour or so of operation. I have a regulator and dessicant dryer installed on mine. Its a good idea! Not hard its all regular air compressor hardware. 150 psi stuff.
I would do it. Shoebox has all the parts available on their site to upgrade older vesions to the latest and greatest as well as rebuild kits for the pistons. Mainly just o rings and bushings. They are very serviceable and there are videos on their web site showing how to do it. In fact spend some time on their site and familiarize yourself with them. http://shoeboxcompressor.com/
I can give you more details on the water removal when you get it if you want. Or you can follow the links on their site for more info on that topic.

Cheers.
 
I'm going to pull the trigger on it. I looked at the videos on SB site and the maintenance seem pretty simple. I will not use it a lot right now because I have a Fire Dept that fill my tanks for free and there's a paintball shop near me that can fill them really cheap. But sometimes changes happen and I wouldn't want to be left scrambling looking for air.