Your best bet would be looking for a duplex and financing it FHA owner occupied with 3.5% down.  

If you come across as rude, you might slow things down.Not sure about a legal time limit but I bet they know more about it and how to get around it, if necessary, than you do....

Best bet is to get inspections and or professionals out to assess the systems and provide estimates.With the roof 20-50 years depending on the climate, area, type of shingle and type of roof.

I Tend to think big and bet on my skills.

There are a lot of great people in the industry (both on the self-management side with various platforms that can help you through managing it on your own, AND on the PM side if you decide to go that route).

After doing some research on Bigger Pockets, I was only able to find investors who utilized Hubzu's platform years ago.

Besides cleaning, and platform advertising expenses are they any other expenses unique to the vrbo strategy to take into consideration?

Probably their best bet is to just deal with the inconvenience and pay the small moving fee - or find a new apartment ran by a more professional operation .

What is your platform and market area

I'll bet you'll have selers and rehabbers jumpin all over.