Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

I personally know several blue-collar millionaires from HVAC techs to plumbers.

Don't be that person.  

With a Conventional Loan you can buy a SFH, Duplex, Triplex or Quadplex with as little as 5% Down if it is your primary residence as long as you have the intention of occupying one of the units for 1 year after closing escrow.This is the strategy I have personally implemented and have assisted many of my investor clients in doing the same. 20% Down is also beneficial as it keeps your payment low but it does limit your ability of buying more real estate faster.i would be more than happy to discuss the different strategies with you over the phone or in person.

The interest rate on a HELOC or Heloan may be better than the personal loan. 

No personal income or tax returns are required.

I have a situation where a person I know is moving out of the country and would be looking to put their home for sale in the summer.

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

Not that it cant or wont, but unlikely.If OP applies for homestead on a new property, then I personally would not lie during the application about receiving the exemption on the existing property.

I tried to create rapport with the owner over the phone but waited to present my real agenda only in person.