I have a rental property that has a negative $150 cash flow and that’s not including repairs that come up occasionally.

If you have the available capital to fund the business to the tune of being able to execute 3+ flip transactions per year, then it might make sense.If you are just seeking a work truck for the occasional flip project, just go out and find something used and inexpensive and pay for it personally.

Airbnb type rentals works decent for me near Anchorage BUT our season is pretty much only the summer w occasional one offs.  

You might have a few dripping faucets and a toilet running occasionally costing you a few hundred extra per month.  

Occasionally, HMLs will allow a high credit score or strong liquidity to help offset lack of experience.

So if I'm a local LO and want my reputation among local Bay Area Realtors to be that my preapproval letter is as good as gold, the wonky ones are full TBD Approvals even if it means I occasionally lose business from one of my fellow perpetually impatient "now now now" instant gratification-seeking millenials. 

Occasionally we have missed on the rents, but not very often.

Occasionally a seller will do an owner financing / seller carryback but not likely in this hot market. 

But occasionally, like when you have two properties on the same street or a duplex, it gets more interesting.

Occasionally we find a listing that is around 200,000 but not often and probably not in the spring/summer selling season.