Secondly, I do not have a high confidence he is still at that address of record, or alive, for that matter.

Outside of real estate, I enjoy spending time with family and friends, playing tennis, traveling. 

Start small and scale up as you gain experience and confidence.

You will also need to understand how to file taxes properly, potentially in both locations, and you will probably need to travel there from time to time, most likely when you do NOT want to go there. 

After asking for status reports, his then assistant would give me a short answer and advise Carson had more to tell me but that he was traveling....always traveling, and that he would call me back upon returning to the office.

Sounds like you've already walked road not yet traveled for some of us.

I invest in the suburbs now becuase I know the areas well enough and feel confident in the values and when I can spot a "good deal."

On Oahu the bottom line of buying in this type of zone is that you will pay higher property taxes and fees, but you have a lot more confidence that you'll be able to continue to operate your property as an STR for years to come.

We are excited to put this together and your input gives us confidence we can finalize this deal with sound legal backing.

will you be traveling to your chosen location in person to supervise and manage your projects?