So I went to sears and I looked at some of their compressors and to be honest I was pretty intimidated. They all needed oil and maintenance at some point to keep running, there were lots of knobs and gauges blah blah blah. Can you tell I'm not a mans man?
(Weird Fact about me: I have always had a fear of things exploding under pressure. To this day I can still be scared of balloons and the like.)
So I decided to check out Walmart while I was in the area (same lot). It turns out the had the Campbell Hausfeld FP2028. I picked this up and I used it today and I must say it's a gem!
It inflated both of my tires +6 PSI in minutes. It has a gauge on the front that lets you see how much PSI is in the tank. It doesn't come with a locking chuck so I grabbed that for an extra like $5 or so.
All and all I think the entire thing cost me about $60 before tax.
I am very pleased, thanks for all the advice everyone!