You will also want to be sure to keep your eyes and ears open to the possible tax benefits of investing in RE.

I get great tax benefits.

It's pointless→ I want to evaluate how the property is performing NOW→ Where it COULD BE performing→ And WHAT it will take to get there.This involves (at a minimum) checking comps, creating a 5 year proforma, verifying taxes & insurance, and making assumptions about the business plan.You can't determine if a deal is a pass/go simply from NOI / Cap Rate.The art of underwriting involves finding value where others miss.If you're passing on deals just from dividing the in-place NOI by a cap rate, send those over here!

Are there ways to tell if one area of a major city is appreciating in value vs another area (besides picking a dozen properties and analyzing zillow estimates (or sales comps/tax assesments, etc) ?

I honestly belief that investors should stop looking for specic catagoeries/situations of people to find houses to buy, and instead focus on motivation (regardless is their house is vacant, tax liened, foreclosure etc. etc.)Do you really care that you get a vacant house deal, or do you care that you find a high profit deal regardless whether it is a vacant house or not?

"Commercial" is meaningless for taxes.

Do they include property tax and estimated income tax from the projected profit?

As to the issue of captive insurance subs, I worked in the accounting department of a small insurance carrier, set up primarily as a tax shelter.

I furthered my education by reading "Writing Winning Business Plans" by Garrett Sutton, "Tax-Free Wealth" by Tom Wheelwright, and, naturally, "The Book on Rental Property Investing" by Brandon Turner.

Sellers aren't always aware of liens or back taxes owed.