Hi, so I won a tax deed at an auction for a vacant lot but I am trying to determine if there are a bunch of leins on it.

Most Jumbo lenders use IRS returns net number so be careful filing your 2023 tax return in not making the expenses total greater than 25% of income which will generally be the hit on gross rents. 

So you will need to know the rules where you work, as well as know the sales tax requirements, for where you are working.

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

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

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.

When you transfer money from your business banking account to your personal account, the IRS will see this as income, and you will be taxed accordingly.

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 also gain the mortgage pay-down in equity and the tax advantages of real estate to offset my gains. 

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