Today he told me he can't afford it, he can't afford the rent this month, and he got in an accident and he's waiting on a settlement...The good news is I'm in contact with a great property management company and I've signed an initial agreement to have them take over on June 1st.  

per divorce settlement/paperwork?

Denise,Presuming the tax lien is redeemed at settlement, does clear title then convey?

During eviction proceedings, we came up with a settlement that she would pay an extra 200/month until she is caught up.  

As long as you settle on the property before any pending tax action is final, you would just pay the back taxes at settlement.

I think the agent is being short sited in not negotiating a settlement to satisfy both sides of this. 

Here is a case from the HUD website from 2013 for a Virginia company that had to pay a $82,500 settlement because they refused to rent to a Hispanic woman who didn't speak English.The Fair Housing Act prohibits discrimination in the rental of housing on the basis of national origin.

Then I'd get them to sign the agreement, and make sure it says it's a settlement agreement and the tenant is waiving any rights to the normal security deposit timelines, etc., to avoid eviction and a court record, etc.

I'm not interested in revisiting the figures of entry for the market of 2009 but will only say the estimated ARV provided by the selling company's hired appraiser who of course I paid for at settlement was in the low eighties.

Plus, it then delays the eviction.What you could do is write up a settlement agreement for the tenant saying you will agree not to press charges or sue her for writing a check without sufficient funds, if she is gone by the weekend and leaves the place clean (or some version of that).