Looks like decisions were made and money spent, but figured I would go ahead and throw in my 2 cents for future readers with similar considerations..
First, I think as to the shocks, there are arguments for both and I don't think either is drastically better than the other. I will say that on my JKU, I had the Ranchos and swapped to the Bilstein 5100's, and have been happy with the decision. They were stiffer at the beginning (which I actually liked) but loosened up some after the first trip with some weight and flexing.
As to the winch, I echo the sentiments of getting a synthetic rope, whichever you go with, if it's in the budget. When I bought mine, I was stretching the budget a bit to get a winch at all, but was preparing for a trip with a lot of solo travel and I opted for the additional piece of mind and got the steel cable. I am now looking at upgrading, but will do just the line and fairlead, so it's not as much of a hit as buying the whole thing at once. As far as brand, I am also a believer in spending more for a quality product, and if the budget is there would go for the Warn too. That said, I have the Smitty XRC and it has done the job well. Of course, I have only actually 'needed' it twice, but still pull the line to clean and lube after trips, and test it before going out.
As for Air.. I have had my current Viair 88P since Jan '17 (~2.5 years) and have never had an issue with it. It has been primarily used for my Jeep (35x12.50x17) and has worked just fine though I will add a couple caveats; 1. Most of the time I air down it's for mild stuff, and I only drop to ~20PSI. Since I normally run about 30PSI in them on the street, I can fill all four before needing to give the compressor a rest. When I have gone really low (around 10PSI) I have done it in stages, since in those cases I usually only had to go so low for a couple obstacles and brought them back to ~20 until getting back to blacktop.
I know when I bought it I looked at the duty cycle, and though I don't recall the specs off-hand, I recall I had calculated that as long as I kept the run time under around 15 minutes and rest it if it was taking longer, it should be fine. Using it under those limitations, I have not had an issue after 20+ uses. Of course, it's not the fastest at < 1.5CFM and I have certainly been eyeballing the ARB Twin with its 100% duty cycle and > 6CFMs! My buddy has one in his truck and I actually used his to air up in Moab since it was faster to wait for him to air up his 42's, and use it than to mess with my 88p. :p
But overall, I don't think
@Dustinfromohio made any poor decisions.