Alden Global Capital, known for owning the Chicago Tribune, has invested in Chicago's delinquent property taxes.

I get great tax benefits.

Here's why:- unless you strategically reported your taxes as making 100% income and not reporting an entire loss on your schedule e - you will most likely not find a lender who will qualify you for a HELOC.

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?

Just curious if anyone uses the property's tax assessment in any way when coming up with an MOA when wholesaling vacant land.

I think this makes everything cleaner for taxes, documenting historic rental payments, and legal issues that may arise due to the barter, etc.  

Property taxes with the exception of no income tax states tend to be way, way higher in cold belt states.For development the entitlement process tends to be longer in cold belt states.

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