My insurers reimburse me for what I didn't use; it can take a few weeks for the check to come, but that's just cash flow management then.

If you can take in $1750/month, it seems like it would be worth keeping… at least in the short term.  

Here in OK, investment in general has really picked up, including an influx of cash end buyers.

Total rents at 100% occupancy across the three are $2900 monthly.I'm thinking because the financing terms are soooo attractive that it may be worth the higher risk that comes with the high PITI?

The exception would be if this was already permitted for STR - short term rentals VRBO then it might be worth it based on location.If you just want to buy a home and have a unit to help cover the mortgage I would still insist on lower price point or NO HOA to help get the total mortgage down so that the other unit covers 50% of the overall payment.  

I'm buying all cash, no loan.

I don’t expect to be someone that finds incredibly cheap deals that become worth double what I paid.

If you choose a Direct Premium subscription with Hospitable, you get $5M worth of damage protection (powered by Superhog) on every booking2.

Purchase price: $135,000 Cash invested: $40,000 I purchased this farm as a place to park out tiny house on wheels & to be able to rent out the house on the property to have a cash-flowing primary residence ;) What made you interested in investing in this type of deal?

And by positive, I am, positive cash flow.