I have heard that I should have an LLC for each home but it seems administratively burdensome to have 100 bank accounts and 100 different tax filings, credits cards, checkbooks, etc...

You can run the Osha 30 Hour Course on the background of your computer, obtain acceptable levels of insurance and as long as you don't owe the city of Philadelphia taxes, you can get a General Contractor license in Philadelphia.

What tax benefits might you receive that could potentially offset some of your tax burden with such high income?

You make money and are expected to pay taxes. 

I know this is pretty obvious, but have you tried checking the Montgomery County property tax records or the property tax assessment records online for Silver Spring?

The house probably also has delinquent taxes etc on it as well.

Also, during those 2-3 years you may have to bear to obtain possession, the borrower will probably ignore court orders to pay insurance and property taxes, leaving you out of pocket for those costs.  

Could use some guidance on how to divide the business, taxes, and payouts.

Hi Mandeep,The 100 sq. ft. of exclusive landlord space could be utilized in a Business Use of Home deduction on your personal tax return, accounting for 10% of your home expenses.

So I'm wondering if I maybe messed up when it comes to accounting and taxes while rehabbing a house to rent.