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. 

If you use hard money financing you'll likely have reimbursement style fund control (contractor get paid upon completion of work) and require lien waivers both of which will protect you. 

The topic for the month will be sent out here, in advance, and these will be more be more webinar-style and roundtable events with other investors as guests.

I am considing purchasing a single-family home (resort style with HOA).

Fans and lights are 80's style. 

Fans and lights are 80's style.