I am truly a private lender, (I have a different full time job) and have done lending with one person I know and trust, he came highly recommended.  

Like you, I also value Family, Health, and Personal Growth highly.

I just don't think because it's cheap(say lower B, and C class) outright that it means it's valuable.In a high(er) debt environment, less is more.

Types of investors who want to find hard money lenders include:Investors with high debt-to-income ratiosProperty investors who cannot get a loan from a traditional lender or bankInvestment property developers who need fast access to fundsCommercial property developers who need a bridge loan but cannot get one from a traditional bankSometimes, homeowners facing foreclosure may utilize hard money loans to avoid losing their homes.https://www.biggerpockets.com/blog/how-to-become-a-hard-mone...

I would highly recommend hiring a lawyer to understand the eviction process and to help with the Rental Agreement. 

I know that there are so many (and more effective) ways in which real estate builds wealth rather than just cashflow but still simply trying to wrap my head around the best way to start building my portfolio. 

While the BRRRR strategy is effective, it requires experience in renovation, property management and market analysis.

Plus access to the small beach for the lake.HOA was pretty high and it made it tougher to make a profit plus the board was kind of volatile. 

Not the situation I want when selling.So the risk is low demand in the face of high supply and a cookie-cutter condo.

not much then go for it.. very important then you need to wrap it and stay in control.Would you consider the wrap even if you have high level trust in the individual?