I don't think Im paying my bookeepeer an outrageous amount, although with economies of scale (I have one commercial insurance plan, commerical portfolio loan from a single bank, one bank account, etc) it probably doesn't take the Bookeeper 3x to do my books compared to yours. 

If I leave this amount in Sch-E, I get taxed at ordinary income tax rate at Federal and State level, which along with my regular W2 income can be substantial.

The exact amount varies by lender but is usually around $5,000 or more.Recalculation: After you make the lump sum payment, your lender will recalculate your monthly payments based on the reduced principal balance.

You're running a business...the tenant does not 'inform' you when they will be paying their rent...they are contractually liable for paying at specific amount on a specific day. 

So if you discount a small amount to get rolling, that is something that can work, but don't want to stay low for long.You will start to get the dregs staying at your place and they can do some real damage to the place.

They have failed to renew my entities with the Secretaries of State multiple times, have billed me wrong amounts, and GREATEST OF ALL, have cost my business ~$50K in cumulative TAX PENALTIES due to negligence in filing for a tax extension, failing to walk me through my tax filings and needed payments, and failing to file an abatement promptly.

Base the payment amount so you're in that range.

Welcome to the community and be ready for a huge amount of information at your finger tips.

Do you have other assets you can leverage (like a home equity loan) for that amount?

The amount of downpayment requirement insures buyers having "skin in the game".