As others correctly noted, as a landlord you must look at the big picture and if this happens to be a good tenant who has occupied the unit for a while, has a history of timely payments and has expressed interest in remaining at the property the value in an extension (assuming that is advantageous to you as the landlord) should be placed above your desire to collect rent in a certain method if this particularly tenant has strong desires to make their payments in a different manner....especially if the lease they signed allowed a different payment method.

@Dan AudinoFor path #1, is your eventual goal to rent out the property?

So, if a loss occurs while the property is being repaired or renovated, coverage would apply, correct?

Because when I ran the numbers myself it was a loss of closer to $14K, not $22K, so I want to make sure I am doing it correctly and conservatively. 

Other locals with similar experience had mentioned that this scenario might not be the best fit and it turned out to be correct.

I hope all the best for you and hope to cross paths again someday. 

Make sure you setup your Goals correctly so you are measuring things like phone calls, contact forms, tours scheduled etc., 2.

If I remember correctly, there is a provision for properties with Fannie and Freddie loans to be moved to single-member LLCs after 12 months of seasoning if the only member of the LLC is the owner/borrower on the loan. 

I retired in my mid-50s and live a comfortable life, grateful every day for the path I chose.Looking back, I’m forever thankful to my partner who encouraged me to take that leap of faith and move to Ohio.

Most who get tripped up are those buying the smaller multi-families that don't possess the correct use permit/historical rental license activity.