What are your current goals or challenges in real estate?

Rodrigues' recommendation may change this), but my next question would be, are there any cities/markets where 1 of the following are true: 1) You have family/friends that live there, 2) You travel there frequently (either for vacation, work, etc.), or 3) Somewhere else you've lived before AND know the area well?

This is true in most markets. 

Sometimes I think, well maybe that newby is an expert at draining swamps....or they have a helicopter to reach the landlocked property and want to practice aerial concrete and building material transport.There was a guy on here the other day, challenging me that he could not possibly go look at all the "deals" he was going to buy in Florida for 10c on the $1. 

. :)We definitely want to invest in true vacation rentals as well but this will be a good learning process with not as much risk to start.  

With that in mind, I’m considering purchasing four rental units over the next four years to build a stream of income that could help supplement my retirement by age 68.The challenge I’m facing is that the deals I’ve come across so far don’t make financial sense.

As a rental strategy for non owner occupants, it absolutely is a fantastic way to generate the highest return, that's true.....but also, and most importantly, your screening has to be on point, and without that, it won't be as effective because one bad roommate can ruin the environment for the other roommate tenants. 

If this is true, the good news is that the property is worth more than the loan balance. 

I reeeeeeeally wanted this to be true, too, I wanted to believe him so bad.

They cited insurance reasons, which could very well be true, but many residents felt it as a big "f you" Now folks from outside the community could argue this was an entitled stance from the residents, to feel they had access to this private land when they didn't, and that on the face is certainly true.