Do you want to be a landlord? 

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.

My short term goal(s) in the next few years are to have 4-5 properties (long term), as well as a multi family home.

I might get 100 people contact me about a rental within the first week with 10-20 showing up to see the place and a 5-10 applying.

Well... they are who they are. 

Checklist- all major items should be known up front.  

People that have "amazing deals" outnumber "people that actually have money to execute on them" by a ratio of 10:1 or 15:1.

I'm seeing a lot of people lately trying to force themselves into house hacks without an immediate cash flow/equity play and "banking" on appreciation or rates dropping. 

You’ll need an agent who knows the area well, a solid property manager, reliable contractor connections, and lenders if you plan to use private money.

With one deal under your belt, financing may also be easier this time.