Initially I was worried about having older guests more frequently which is what I have heard about VRBO.

Most buyers and sellers are vulnerable because they don't buy/sell real estate frequently; licensed agents (me) take pride in "guiding and protecting" clients from transactions that can go wrong. 

The problem I see is passive investors frequently don’t invest on a risk-adjusted basis.  

I would avoid Holly Hill, Daytona's ghetto, like the plague because the oldest profession seems to be a major profession there if you know what I mean.The Daytona area is a bit or of my way, and my brother-in-law had frequently complained about finding a nice property that turns out to be in Holly Hill.Nearby Ormond Beach and Port Orange seem like nice communities in comparison.

I am not a fan of using section 8 as a full-on investment strategy.

You will get hassled at customs if you  are travelling frequently, as they deem this as doing business and may require you to get one.  

In the midterm rental community, it is regularly discussed how frequently people inquire about accessible properties, particularly in the highest end insurance placement niche where there is, indeed, a price premium on accessible properties.

I'm curious as to why VG Jason wasn't a fan.

Unless your job is one that you can answer calls, or look at the message frequently to take care of any potential issues that come up quickly.

The issue that I'm facing now is whether I want to pull it out against one of my rentals or on my primary.I have found a bank that will allow me to borrow as a second lien on rentals but their rates are higher than what I could get when just doing it against my primary.What I'm most worried about is what happens in a worst case scenario, should something drastic happen in the market.From what I understand, using the money against a rental doesn't necessarily provide much more of a safety blanket in case things hit the fan because if, somehow, the HELOC lender can't recover their money, you'll get sued anyways.