My experience with Richard Garcia's Real Estate masterclass has been an absolute game changer for me in the world of real estate. 

You probably recoup the 5k in ARV, but Old North Milwaukee is an economically challenge neighborhood, so manage your expectations.Avoiding frequent turnover, tenants who don't pay, damage property or cause other issues is the name of the game to achive long term profitability.

You don't wanna get involved in the Sub2 game.

Investors buy here because of strong jobs, strong rent growth, strong appreciation and the future cash flow but honestly many of my clients are playing the long buy and hold, appreciation game.

I've been in the game for over 20 years, mainly in Tampa, Florida, and it's a fantastic market for both cash flow and appreciation.

this would change the game drastically.. in the amount one could pay for the property at the sale. hope this makes sense.Also @David Krulac stated that these liens get paid in a certain order..

Mail is a numbers game.  

Remember this little nugget: There are 3 things you need to do to win the money game.1.

Everything you suggested was the original game plan the house will be a rental or air bnb and the land was bought with the intentions of having tiny hones put on it.

It sounds like you're ahead of the game here because you're focusing on your local market, which certainly makes things much easier.