I'd start small and think about the least time-consuming and the lowest-risk strategies considering your busy work schedule/ lack of bandwidth to take on an additional job which is basically what real estate investing needs to be in order to be successful. 

In the ideal scenario, we picture keeping the property as a cash flowing asset forever and letting our kids deal with it after we die.BUT, if that doesn't happen, and we decide to sell in 7 years or 10 years, I'm going to kick myself for losing out on the capital gains tax exclusion of $500k.  

Do you provide consumables (toilet paper, coffee, paper towel, etc.) for your clients or do you set aside money for to replenish?

However, if you are going to be using that space for events, etc. or are leasing it to someone who will be, there could be an impact on your policy. 

Or worse, if the project is losing money, do I get my $100,000 back or it's gone forever? 

We bought a large home on a large lot we thought would be our "forever" home for $460k. 

Id line up these steps.1. consume education through books and podcasts.

Contact the Federal Trade Commission and the Consumer Financial Protection Bureau. 

- You can get away with doing it yourself forever.

Unless you can find somebody that isn’t concerned about all the regulations surrounding consumer loans … not suggested.