BTW, i have extra liability insurance, due to no LLC protection.

I want to be proactive for next time, I thinking of budgeting 20% extra on top of the estimate to cover myself from them.

Given you are in Milwaukee where I would assume home prices are still reasonable, you could buy 5 rental properties that would cash flow ~$250 a month each or an extra $15,000 a year total.

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.

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.