The most important macro level factors that I consider are 1.

The end goal is to own 63 properties in 7 university markets with nearly 3,000+ beds. However, the addressable market still consists of more than 6.3 million students in 280 markets, based on my target market of Histo...

It would all depend on your comfort level with the area that the building is in.

My name is Joe Sherman, I have been in the real estate business on a personal level since 1998 when I bought my first home.  

Hit 'em up with your questions - one of the reasons I chose Grand Rapids was the level of support I received from local investors. 

Regarding your question about the 5-year period, I believe you are talking about the built-in-gains (BIG) tax but you may also be talking about Section 351 transfers.The BIG tax allows you to avoid taxation at the highest corporate level on your built in gains when you convert a C Corp to an S Corp as long as you don't sell the property or otherwise recognize those gains within a five year period.

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!