Hey I've represented commercial multifam landlords and we've never really run into issues with CityFHEPS payments.

The issue I'm having is that the house doesn't cashflow unless I pay down the PMI and refinance.

The issue with purchasing the property and then transferring the property into an LLC are the added transactional costs.

Yeah..ok...And all teachers should have kids first...All doctors should have lots of medical issues before they can practice....All dentists should have lot of dental issues before they can practice...Every waiter should owner a restaurant before they can wait tables....Every car salesman should have bought multiple new cars before selling any....I get your point..... it would be great if every realtor had to have real life home ownership under their belt, so they have that BTDT experience..... but not gonna happen

Are there any issues with this strategy? 

@Dequan AllenA beneficial tactic for those trying to accumulate riches and become financially independent is house hacking.

Real estate rental investing is what I want to do, I don't want to have to work a job I don't enjoy for years just to accumulate some savings.

We  manage inventory , are hospitable and curious with your guests , manage any maintenance issues and prep rooms for the next guests while  insure you obtain or maintain a Superhost status  -- I think that is very a fair tradeoff , If you listing cant afford that 15-18% than maybe that property is not pulling the numbers it ought to be. 

There are facebook groups where other Ownwerrez users help each other with issues. 

The issue now is that I'm not sure if I bid on a second mortgage or if there are multiple mortgages on the property.