Fear does not keep me from buying a can of spray paint and running up and down a neighborhood toward the end of a rehab covering up gang graffiti. 

I'm not a socialist, but health care is a special case where it would make sense for the feds to "regulate commerce" for the benefit of the people.And back to real estate...I hope your RE investments cover you in the event of a catastrophic health event.

Understand "why" you want real estate and write down your goalsNo TVNo radioNo social mediaNo games (except family stuff)Turn your car into a mobile university (podcasts, audio books)Get up earlyEat a simple diet (simplicity and mind-share)Keep a simple wardrobe (simplicity and mind-share)Give up social stuff for a year or twoSchedule specific time with your wife and kidsCut out spending that does not align with your goals (requires less income to cover)Tie your identity to growth (mindset)It's time to attack the day (every one of them).

The longer it takes, the longer you're paying the mortgage (if you financed) without any rental income to cover it.BUT when it's done, if it's done well, you have a property worth $200k that you only put $150k into, for example.

All my bases are covered.

If you raise the rents and the tenant can no longer afford the unit because their voucher will not cover the difference, that is another reason a tenant might move.

Enough cash flow to cover my personal monthly expenses, create financial freedom, early retirement...I really just want to keep building this monster!

The expectation would be that I can at least do 4 flips a year (average $30K) to cover our living expenses and let the rental income build up the cash reserves month-over-month for vacancy, repairs, capital expenditures, etc.; however it would be a safety net from month to month, if needed.Request: I want to know any and all of the possible financial or other real estate investing issues that I might come up against that I need to be prepared for that could put me in a precarious financial situation.So please, unload any and all possible events that would make this scenario something that would put my financial situation at risk.Thanks for your time!

It depends on what the HOA covers.

I suggest checking out some of the webinars that BP puts on, @Brandon Turner covers deal analysis very well.