The problem I am running into is my brother is old school (work for a company for 30 years retire with a pension) and is convinced I would only make the same mistake again.

Un-leveraged real estate can yield buckets of monthly cold hard cash to live or retire on.

(once a year their shop guy calls for us to pick up, and dads been retired 3 yrs)So we then would mix say 50 gallons up in a large vat...

If I were retiring, I would take a more conservative approach.  

Taxable social security and tier 1 railroad retirement benefits.Deductible contributions to individual retirement accounts (IRAs) and section 501(c)(18) pension plans.The exclusion from income of interest from qualified U.S. savings bonds used to pay qualified higher education expenses.The exclusion from income of amounts received from an employer's adoption assistance program.Passive activity income or loss included on Form 8582.Any rental real estate loss allowed because you materially participated in the rental activity as a Real Estate Professional (as discussed later, under Activities That Aren’t Passive Activities ).

(don't know too much about commercial so those goals are blurry)All in all the big end of the road goal is to have 250,000 dollars a month in net rental income long after I've retired from my 9 to 5.

My parents have recently moved to Wilson, NC where they rent a home to be closer to family now that my father has retired.  

There is no need to replace my income with rentals and in fact my goals totally changed to "wealth building", "college saving", and "retirement saving" RATHER than wanting or needing any cash flow NOW.

I have an opportunity to buy 10 houses around a college due to owner wanting to retire due to age and working on some charity programs that he and his wife have started.  

If nothing else, the owners address might be a clue too as I live in Pennsylvania and many people move to Florida or somewhere else in the south upon retiring.