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...

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.  

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

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

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?

You make money and are expected to pay taxes. 

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

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

The purpose of course, is to save for retirement in either a deferred or tax free account. 

Look up local ordinances, laws, taxes, and insurance.