Hudson provides umbrella insurance for home/auto and 12 rentals.

This is where you take a portion of your annual auto expenses (not just this one trip!)

It has the ability to set up custom workflow, manage documents (including a doc portal for borrowers to upload), servicing management, auto-document generation, and email templating for streamlined communications with vendors like title and escrow, insurance agents, borrowers, and investors. 

I'm ok with month to month, but I also need to raise rent to current market value, add in late fees, set up auto pay, etc. 

I have the housing commission auto-deposit the rent into my LLC business account.

It takes a tremendous amount of force and energy to move the train but once its started its on auto pilot (metaphorically).

If you can qualify based on all three of these regardless of how you move forward once the auto lease ends, you have nothing to worry about. 

Not convinced it’s worth $390/yr and want to cancel before it auto renews.

My rent is $740 a month, which I had set up on auto pay monthly.

While different sponsors, still not really diversifying - it’s like investing in one type of stock company - for example airlines or auto industry.