I talked to 2 other neighbors who also have rooftop units and they aren't experiencing vibration/sound as bad as I am.

I know that for some of you this will be elementary, but many on BP are not in finance.

There are a few blocks that are being developed with what seem to be over-improved houses (large town homes listed at over $500,000, with parking, rooftop decks, etc).

We are bunch of friends who decided to pool some resources and I happen to be the tech savvy one with a Bachelor in Finance, aka the nerd.

This is the best education I have ever had ( I also have BS in MGMT and MBA in finance), but still RE education and getting my license so I could be not dependent on anybody was one of my 10 best decisions in life.

Any other things I can have him check when he goes on to the roof top?

Keep in mind, the homes here are really not that special, most are quite cookie-cutter, we have no moutain views or isolated cabins or roof top penthouses.

My background is in Finance & Engineering and I enjoy the deal analysis stage but am ready to formally starting searching for that first property.

Or in finance terms cap rate>interest rate. 

I looked at a property advertised this way, the owner was using comps for apartment buildings that had pools, in-unit laundry, gyms, rooftop decks, etc.. but trying to sell a rundown 12 unit building, no laundry at all, no pool, gym, or anything, but telling potential buyers rent for 2 bedrooms in the area are comparable.3) Make sure to take a look at the leases if you're going to try going the route of not renewing leases, then doing a rehab, and lease-up at higher rents.