I want to start by wholesaling just to get my feet wet, establish relationships and build capital and eventually buy and hold.

My dream is to eventually become financially independent from monthly income generated by a portfolio of rental properties.

Eventually I would like to obtain a couple rental properties and maybe even do fix and flips. 

And SOOOO many people who arent truly motivated.By asking all the right questions and getting as much information as possible you can usually tell if someone is motivated enough for you to make a meeting to see the house.You will eventually get a feel for this, however, your instincts arent always 100% correct either.

I am in the insurance business by day so I will be wholesaling part-time eventually transitioning into RE full time.

Eventually, this investor sold the entire portfolio and went back into buying single family homes without HOAs. 

But because the money “eventually” showed up, I was lazy and let it slide until it had slid too far.I did learn that I do like real estate investing, despite the way this one turned out and decided to do another deal a bit closer to home, where I learned a bunch more lessons.

I just have questions that I would like to have answered before i spend any time or money on something that would eventually have my named tarnished or worse, land me in jail. 

Eventually, I also would like to grow into some other markets where I have people I trust on the ground. 

and then eventually produces a form to sign in which coverage is declined.It's uncommon but totally legit.I like the advice of @Jon Holdman if that tactic is available where you do business.