I've personally found the bulk of my Chicago purchases off the MLS.

You are not allowed to compound interest.If you bought the certificate from the state on a best price offer, you charge interest on your purchase price, not on the full amount of the taxes that were due, but were not paid by you when you purchased.After you obtained your tax deed, you are entitled to something called "mesne profits" if you file an ejectment lawsuit against the former owner and they redeem during that lawsuit.  

I'm 53, married with 2 kids less than 17 years old with debt only from purchases on credit cards and my home.

Financing depends on your scenario and what type of property you're purchasing.

I’m considering either buying a rental since it’s cheaper or purchasing a flip if the market is booming enough.

My plan is to sell my primary home in New York and purchase a house to live in South Carolina.

You owe two taxes:A. capital gain tax on $150k ($500k sale - $350k purchase)  PLUSB. depreciation recapture on $100k of depreciation taken.Now, let's assume that you messed up somewhere along the way, and you only took $70k worth of depreciation instead of $100k.

Purchase price: $380,000 Cash invested: $135,000 Annual rental to be turned into STR when tenant vacates What made you interested in investing in this type of deal?

Purchase price: $360,000 We bought this stacked duplex, lived in one unit for 2 years and moved on.

I have a proven track record of being able to identify a property, make the appropriate repairs, and have an ARV that exceeds the cost of purchase and repair.