I have a park with some extra land, I can explore this idea too. 

Should I ask the bank for an extra amount (maybe 1.5x my estimated repair costs) to cover for incidentals? 

if you want to just blow tons of extra money and do it that way you can or you can be a little bit smarter and avoid all that.

I would try to work with the tenant and make a payment plan to get the higher deposit or increase the rent to market value (If your market support it) and not asking for extra deposit.I have a 7 month old puppy in my own house and when she was younger she did some damage (Chew some drywall and trim (But she's still cute :) )) but she grew out of that phase.

High end properties will have a hard time getting the market rent as Section 8 pays by bedroom and doesnt pay extra for nice finishes etc.

And with appreciation slowing, it may take years to earn 20% equity and refinance out of the MI.

I am eligible through the city of Pittsburgh's Urban Redevelopment Program for a $20k, 20 year, 0% interest loan and possibly an extra $10k for utilities due to low income. 

I am eligible through the city of Pittsburgh's Urban Redevelopment Program for a $20k, 20 year, 0% interest loan and possibly an extra $10k for utilities due to low income.

Are their extra steps involved to be sure nobody else is an heir to the property?

How much extra rent will the pool give?