I've had a Craigslist rental ad up for weeks with no issues, no discriminatory verbiage, etc and since I had a "run in" with a local RE agent who was trying to force me to take her applicant (who was on every program in the book; not that there is anything wrong with that) I believe she is behind the flagging since I wouldn't accept the applicant.  

Unfortunately, it's not just the first month the tenant is on assistance, it's becoming an every month issue for some tenants.

Pretty rare from what I see that cities allow or want this....turns single family neighborhood into multi family and most of the zoning people don't like this.Plenty of issues from their point of few of why they don't like it.....parking is one...now no one parking in garage, and potential for more cars...so now 3-4-5 cars in the street.More taxing on the water/sewer/trash/police/fire/city services.I wish you the best of luck with this. 

Investment Info:Large multi-family (5+ units) other investment.

Investment Info:Small multi-family (2-4 units) buy & hold investment.

The issue I have and seen being thru several hurricanes in Florida is that once a hurricane passed and there is damage, most contractor's raise their fees as well as materials.

If you're utilizing the house hack and low downpayment, I wouldn't think you'd have any issue hitting that target for a Cash on Cash or IRR.

Were you targeting a single family home or multi-family property? 

I recently started wholesaling real estate in the last 90 days, and I am looking to expand our business into multi family commercial as we have some cash flow now. 

It's an issue.