@Devin James, clearly the only opinion that matters is the buyers.  

I don’t think that would be an unpopular opinion.  

I would say this was the least organized BPCon (no cevent App, poor email distribution, my workshop that was $300 had about 20% attendance rate) I have been to, with the worse room problems (both ac and hot water problems in my room), and the hurricane issue (they cancelled the meal but many of the restaurants required reservations that we did not make because we were expecting the meal), and in my opinion worse keynote speakers even when one was a repeat (I like David Greene keynotes, but …), I enjoyed this BPCon more than the others I attended. 

If they stay more than five days, I recommend treating it somewhere during their stay.There are a lot of guides on youtube or Google specific to short-term rentals.I appreciate @Nathan Gesner opinion and there are a lot of people that do share his opinion.  

Now we're seeing investors pouring money into buying Class C rentals - but, many are getting burned.In our experience & opinion, the main determinant of property Class is not location or even property condition, those are #2 and #3.

Here’s our OPINION for the Metro Detroit market (use as a template for your target area!)

You’ll probably want an opinion of title at a minimum and a much “safer” course is title insurance on both properties.  

In my opinion, the short answer is to use your cash and refinance it into a 'standard' loan if you are going to rent it or sell it when you are done. 

You ask for advice and someone gives their opinion. 

I am not defending either party just stating my opinions.