If you decide to go the multifamily route, Real Estate lab .com is a multifamily software for deal analysis plus they have many other useful features. 

4) What do their places look like, how do they feature their professional pictures?

They even added a small “welcome basket” with loccal treats, and guests loved the personal touch.. it became one of their most mentioned features in reviews!

You’ll want to get loans from local banks and credit unions but you may run into issues with more limited features.

For example we helped a client acquire a $1.5M oceanfront home that is pushing $180-200K per year and a $875k home (with no water feature) generating $125k gross revenue annually

-Structural (foundation, wall, ceiling and floor)-Roof and Exterior(Roof Condition,Gutters and Downspouts, Siding, Windows and Doors)-Plumbing (Water Pressure,Leaks, Drainage, Pipes)-Electrical (Wiring,Outlets and Switches,Breaker Panel, Lighting Fixtures)-HVAC(Air Ducts, heating and cooling)-Water and Moisture Issues(Attic, Mold and Mildew)-Kitchen and Appliances-Bathrooms-Pest and Insect Problems-Safety Features

These loan products include a partial release feature that allows them to be repaid gradually as TIC interests are sold, and ensure that the sold TIC units are not encumbered by a blanket encumbrance.- The variety of financing products available as individual tenant in common loans remains limited, and the terms are generally less favorable than either apartment building loans or condominium loans.

The property features a shared dock, 3000 sq ft of decking, and a fire pit for each cabin.What made you interested in investing in this type of deal?

I recommend homing in on what MOST vacationers are looking for in a specific market and try to find properties that have natural features/amenities that are scarce.  

Quote from @Lorraine Hadden: Take these California Malls ---- Eastmont Mall - Closed (Oakland); Carousel Mall - Closed (San Bernardino); Laguna Hills Mall - Closed (which was featured in BACK TO THE FUTURE); and the Village at Orange - Closed.