And what they do is put them into their own "Credit Repair" program (which from what I can tell is just producing a series of letters to Credit Agencies as well as probably other tactics involving "positive credit" which is a conversation for another day)...but is my assessment on Rent-To-Own Correct?

When I search through the DC real property assessment database I discovered that alot of the vacant homeowners have $10,000+ in back taxes.

Appraised (assessed, you really mean) property tax value is worthless for determining market value.

You don't want to be surprised with a special assessment because the roof needs to be replaced and they have no reserves.

Is that the tax assessment?

-I've been reading a lot on here about how to handle security deposits when it comes time to assess damage and determine what is normal wear and tear and what is "damage" that can be charged against the security deposit.

Not much, for independent appraisers, depends on who you can work with and the market.While we usually think of appraisers doing value assessments for RE sales, there are other reasons property is valued.Trust administrators, may need annual reports of value.

Also, are there any assessments on the horizon?

I need to know who much is reasonable, is it a common assessment, can we do it; even if is not listed in the CC&R's and can you implement such an action by stipulating that it will be added to the CC&R's.

Also, I see that you have HOA fees so you have to be prepared for special assessments which will add to your costs.Good to see you take action.