One of my properties has also been booked a few times for photo shoots for clothing and other products.My advise to get started is pump the brakes and learn A LOT about underwriting and managing an STR. 

Yours may be a brand new, high-end, fully upgraded, highly sought after style, with a huge lot and the other one could be a dilapidated 100yr old, needing to be rebuilt, on a tiny lot. 

I got one of my clients closed on a east Medford home with two ADU’s that was an older craftsman style home that they’re househacking short term rental market and it’s been great for them!

For example, i had one that in process clients selected a garage door style that literally did not exist at the time.

Same style of property and the dates youre looking for.

Conventional Buyer - these people love houses, they like trendy modern styles, and a house is one if not the biggest purchase they ever make.

I can try to stay around 10% down and finance both buildings as one property via investment/commercial style loans or I can subdivide the property into 2 seperate parcells, take an FHA on one building and live in a unit, and try some other low down payment loan on the other building.

Some only work in certain price ranges and styles of house. 

Yes there is an over saturation in Vacation rental markets, but with the right amenities, stylings and hospitality experience a differentiation can be established resulting in consistent ROI.  

I have also seen people rent out SFH to multiple people similar to a house hacking style.