From a high level, figure out what means retiring to you.

Probably the best ways to get started depending on your cash level is to wholesale or do Fix and Flip.  

I would call that middle class at least, and that's assuming 0% interest on that initial $3.5M.So, you're ***-u-me-ing perfect health, no injuries / accidents, no natural catastrophes (hurricanes / cyclones, wild fires, volcanic eruptions, ... at least two of which are common in HI), vehicles which last forever and never need to be replaced, destruction-proof housing and furnishings, ...... and if you CAN live that lifestyle in HI on $100K / yr (most people can't in ANY state), why are you not teaching personal finance at the university level? 

The meetings are always full of like-minded investors of all experience levels and it's a very comfortable place to make new contacts no matter how much experience you have.Hope you enjoy the meeting!

I am hoping to begin investing within the next few months and I am sure as I dig deeper, more and more questions will arise.

I'm subject to FDCPA rules on a Federal level and similar rules on a state level (Depending on the state).

When you gain a comfort level you may offer someone a loan secured by their investment.

Some of the issues brought to our attention by current tenant would need to be addressed by the seller before acquisition.There is a potential piping issue or cracked pipe somewhere as the tenant complained about some water level problems.  

Also, you'll never learn with the same level of interest as when it's your money at risk.

The market is really hot right now at a national level.