You can find deals that are great numerically but could lose money and you end up suffering frustration because of terrible tenants due to non-numeric information.Real Estate requires people (Seller/Renter/Buyer/Property Manager/Contractors) and those are less plot-able on a graph.Just don't want you to get stuck on making a complicated spreadsheet :)

I often found myself so pre-occupied listening to success stories that I barely consider the numerous, obscure cases that never made it. 

appreciation comes in many forms.. its not all gambling and hope.. 

And a Heloc would help with this, because they know you can draw the equity out of your home and go on a expensive vacation, or gamble it away or whatever.

So- here I am 6 months later trying to figure this out- I’ve met numerous people that own Airbnb’s and have had ZERO problems- but I am hesitant/confused because even the people in the government offices are confused- 

Gambling on a market is dangerous I think, but that's what gambling is all about.  

Exactly @Bill F.and @Joe Splitrock, No matter what our individual opinions are on this, or how invested we are in STR's, it's no longer debatable whether or not STR's are to be regulated like hotel businesses because all of this has been settled in court already numerous times, and AirBNB has lost nearly every case.

A lot of people argue that Hawaii of all places will be paradise and prices should always go up but I consider that gambling.

Living in a place free and clear would be awesome, but I’ve heard numerous times that recessions are where people can start building wealth.

There are numerous investment options and many are returning better than what the majority of recent RE investors are achieving.