From my part, I analyze the property's location, neighborhood growth, appreciation factor, the average rents using some paid tools, and crunch some numbers for them to let them know the CoC return, cash flow, and more etc.

It costs big money to place a resident - often a 100% of the first month's rent.

Days rented is down 30% roughly. 

Then renting them to Section 8 Tenants.   

Keep it and shoot for a high rent 

We are just wrapping up on the rehab and plan to rent it out in about a month.  

However, she asked me if I accept the rent assistance.

I have in the past hooked up cameras and paid for wifi until the house sold or rented, but setting  up and then cancelling the service was very expensive too.

Not sure what the market is like in Milwaukee but in North Carolina, rents are declining at about a 1.5- 2% rate YoY and with the supply increasing, it seems as though they're not tapering off yet. 

This doesn't mean that you shouldn't be ambitious with your objectives, as long as you're realistic.I have years of experience with short-term rentals in Mexico but I'm not sure how useful that can be to you since I invest in beach markets where there is mass tourism and visitors rent for one or multiple weeks so it's fairly different.