While I don’t yet have personal experience with a HELOC, I’ve thought about this one for my self many times.

He has millions of dollars invested in his property and must be extremely careful that he doesnt't rent it to a person who is a crazy failure.

Not really worth the time for me.As someone who has written a bunch of algorithms over the years, I am pretty sure there is much more that goes into the results for each person other than the obvious.

Admittedly, they seem a bit sketchy,My question would be, for a person such as my self, how does one go about vetting these syndicates?  

Some areas are higher end for personal use while others are primarily for short term rentals.

Quote from @Stuart Udis: Unfortunately there's a ton of online content teaching novice investors that reaching XYZ number of doors equates to financial independence.

The properties I won are nearly impossible to find on the county tax sites with the information given and so far the person is not really helping. 

If your tenant starts a kitchen fire and the insurance provider finds out it was a rental, they will deny your claim.Landlord insurance still covers the property, but won't cover your personal belongings since you live elsewhere.

I can say my personal experience has been pretty mediocre.

At a minimum,  you should understand what the current zoning is and what restrictions there are.As the post above mentioned reaching out or going in person to speak with the planning and zoning department will be very helpful.