How can I analyze if that will allow me to charge in excess of that amount to the tenants (ex. $+200/ mo rent).

Seniors on fixed income with no other income than Social Security DO NOT qualify for food stamps (excess income, if you can believe it!)

If getting properties free and clear is the goal, use the excess cashflow to paydown principal if you want - this is the most "safe" option as it will allow you to add more payments and also give you breathing room if you have unforeseen events (personal or in the portfolio).  

What is your appetite for rehab?

  $90 per unit is extremely excessive and would nearly be the cost of your PM.

I would maybe ask the person sending these emails (if through the meditator or not) if there was a particular instance that they were upset about that you could resolve - did they have too much to drink maybe and tromped through  her flower garden, were they excessively loud and kept her young children awake etc. - is there a resolvable issue you can fix to appease her until you get these last bookings through? 

But long term if they want to grow, beyond just wealthy/wealthier investors, they'd probably want to support more than 1/8 share ownership.With the current model and pricing, it doesn't make sense to me to make that kind of investment unless I had excess money to spend.

I am looking to reach the audience that has an appetite for $700k in free cash flow 

One of our local store's had excess landscaping rock in front. 

If I live in the other unit, it would have to pay 5,000 per month, which is a bit excessive for me.I want to buy this place because it's my dream house.