How much are the reserves for the HOA (inadequate reserves mean that fees will be going up)?

A class properties can help decrease maintenance and may rent faster, but the returns are going to be lower.  

Ahhh nice job being honest and transparent, @Michael King You may want to use "reluctant buyer" and "appeal to a higher authority".And use "I'm not sure this idea makes sense, and I'd have to have my business partner look over the numbers (appeal to a higher authority) but WHAT IF I could give you a payment for a period of time, this payment would cover and part of that payment would be decreased from the purchase price in the future.You did not ask the existing financing question, if the property is free and clear, you could position yourself to an installment sale, offer more than the seller wants but your terms of note structure and your payment amount.I'm happy to talk to you about the negotiation.Remember, older people want to leave a legacy, and they think about death.And I have a thread about this here.http://www.biggerpockets.com/forums/83/topics/1670...

We have been able to decrease vacancy/expense and have no management fee.

Wouldn't other prospective buyers who know that a new roof is needed just decrease their offer accordingly?  

HUD funding here has decreased a little over the last couple of years with the sequester and stuff.  

According to Nationwide, a value of 100 for the LIHHM suggests a healthy housing market, and the likelihood of a downturn decreases the higher the value climbs above 100.

A single property is going to decrease your operating costs and make the property more profitable.The other reason, is that closing costs are going to start adding up with more properties.

I don't want to convey favoritism or desperation but I also want to decrease vacancy. 

Sometimes the ambiance of a place will decrease your rental rates or your amenities don't meet the needs of higher quality tenants.Cap rates are at an all time low if you want to sell.