The main house is original (this place was built in 1924, very cool) and we rent it for $1,650/month.

That leaves me with 2 houses, both rented but one of them needs to go too.All this is close to the end of a dead end street.

In total, including money lost from rent, legal fees, and repairs, the situation cost almost $30k.

So this reason I rented the unit.

If rents don't increase faster than inflation, you won't have sufficient funds to cope with rising costs.

and I also rent to voucher holders in the Milwaukee market. 

Loss of Use / Loss of Rents: Normally, there is a 20% included limit.

Rents in the area are strong, do you think it makes sense as a rental, or would you go all-in on the flip? 

I exited the market due to the short term rental regulations - properties that are rented under 90 days are considered short term.

in 3 years you can pay off any mortgage 500,000 or less for $1,500 bucks.. or in 5 years a $477,000 mortgage for $100..I am implementing something new for the real estate industry, primarily to mortgage holders & the rent to own industry, as a shorter-term approach to be mortgage free, without cost being an obstacle ..