I was into it for $25k and put $15k make it rent ready.

I would think about other options.1) Extension with current lender.2) Sell/rent - depending on the condition ?

Does anyone use biweekly rent payment schedule for tenants? 

My provisional strategy is to put a room in a property up for rent while also living in it as my primary residence for a year. 

It's wrong.Also, with inflation being what it is, rentals scarce, etc. people cannot afford to be paying for multiple rental applications.

Look in to see if you can get a 2-4 plex or a SF house that you could rent out other rooms to friends, etc..Good luck!

Have you thought about trading the fiveplex for a Class B duplex in a Class B neighborhood and move into one of the units and rent out the other??

Randy I believe exactly what you are saying, I think I will come out ahead.Fortunately, I had a good insurance agent who gave me multiple riders like Actual Lost Rents, Code improvements, and a few others.

We originally rented out a single room in the home to house hack, but after a career change and a bug move we decided to turn the house into a single-family rental situation.

The most obvious is that you will be able to offset your mortgage with renting out a few rooms.