On that shear; I find it hard to believe that they would rate it at "up to 14 ga mild steel" That's just way too optimistic, or misleading. When that design was first marketed by KETT back in the 70s our hot rod club bought one. I don't recall what the max capicity was, but I doubt it was more than 18 ga. Ours broke when one guy was cutting an old panel off and just barely hit an area that was a lap/double seam. If you get it fixed, I wouldn't use it on anything thicker that 18. JMO. If you have an old fashioned pair of long-handle tin snips, you can get an idea of just how much force it takes to cut 18ga, never mind how tuff 16ga is
That drier/regulator should help with some moisture. OldRed was referring to the old threads on this site where you can get info on how to run metal pipes or homemade coolers to eliminate a lot of moisture in very humid conditions. On very humid days the moisture will condense (in large amounts!) in the rubber hose that lays on the cool garage floor as you run the compressor full tilt. After real heavy use on a very humid day, the puddles of water in the line will be too much for any in-line filter type drier like that. It should be OK on dry days.
On the compressor, yes it is marginal but you will know more about it when you get into priming large areas next year. As with anyone on a tight budget, you need to "work with what you got", and try to work around the limitations