While I wouldn't need to make a too much to supplement my retirement income, I definitely like the process of REI, and would like to explore some additional avenues like getting my RE license or possibly look at doing financing.  

I'll most likely end up with a generic, flat roof, red brick quadplex built between 1920 and 1960, give or take. 

The cheaper alternatives out there are akin to purchasing a set of generic divorce filings online and filling in the blanks.  5 - it may be possible for an inexperienced sponsor to team up with an experienced sponsor to get a deal done - but - the inexperienced sponsor will likely have to settle for a relatively small ‘success’ fee, and have to count experience gained as their biggest return If you don’t use Reg D and rely on the general exemption then you can do no “general advertising or solicitation”  Reg D 504 b also doesn’t allow advertising, 506 c does allow it.  

Thanks.Mike Between the title insurance policy and your homeowner's insurance policy, you're pretty well covered, but by all means ask your go-to insurance guy what specific stuff his policy covers, and ask your escrow officer what stuff her policy covers.Location specific natural disasters often are not covered by the generic policies, earthquakes in the case of CA and...

You will need a longer history of earning those variable income types if using a degree to supplement your work history.As mentioned above, if you truly want to buy an investment and you won't be living in the home,  investment properties don't qualify for FHA loans.

We BRRRR 8-10 peryear and the flips supplement and money left in the BRRRRs.How do we choosewhich ones to BRRRR?

Building a note investment business that generates monthly cash flow of at least $1K a month within the next 5 years to supplement my expected other sources retirement income is my current goal. 

I don't see too much of an issue of negative cashflow when it comes to a house hack if your intention from the start is to treat a similar property as your residence along with your abilities to afford the expenses without any rental income as a supplement.

Looking to buy a cheap property to start my path to financial freedom via supplemental income.

We supplement during the colder months with heavy blankets that are kept separate from the bedding.