I have a conditional approval for $10,000  to complete work on a fix and flip I started, and had to stop because of the hidden damage I ran into.   

Its like a snow ball effect.

How have others effectively dealt with these types of HOA situations?

I will sell it to him for $1He agreed to pay $12,500 in 12 months to cover the money I have invested in it ( Down payment)  and some 3,000 Profit For MeHe also agreed to pay all the utilities, and all repairs, damages that the house may need, now and later.  

If FoxConn happens it is so big, it does not matter where you are, ripple and displacement effects will raise the tide for all boats in the greater Milwaukee metro area.

Unit is in good overall condition, one interior door is damage, and a few small holes - $32K MLS-2180280482123 Dawnlight Ave - 2 BR Flat - Rented $615/month - Great condition, home has been converted to baseboard heat.

Explain that you understand the penalties of trying to go around an agent (you get sued and have to pay them damages) and that you have no interest in going around them. 

As Irena Belkofer stated, it gives them the most incentive to take care of the unit, where as some tenants may figure they don't need to bother as the fee covers all the damage. 

FYI Maryland requires third parties to rely upon a properly executed, witnessed and notarized POA... subject to damages if they refuse.

Find a good inspector that is trusted by professionals in your area and get a good pulse on the effective life of your big ticket items (Roof, HVAC, HW heater, etc.) and calculate out how much each will cost to replace, then do the math backwards for what you need to put aside for CAPex and maintenance.