I get a lot of free education too, but as supplemental education...not as the core. 

Do you need the cash flow now to supplement your income or are you looking for more of an appreciation play?

If you have a below market rent for a good tenant, but have to place a new tenant that inherits the rent base of the existing tenant then you are supplementing a new tenant of unknown quality.In part due to rent control, reduced rents even on non-commercial MF (4 units and less) does affect the value of the property if you need to exit for any reason. 

Here is my plan: - Purchase a distressed SFH using a conventional loan (5% down)- Live in that property for 6-12 months while rehabbing it- Cash our refinance - Purchase another SFH as my new primary residence and plan to live there for 3-5 years- Rent out the initial SFH and cashflow a reasonable amount - Continue to save money from working + build equity in the initial SFH- Leverage a 1031 exchange to sell the initial SFH for a distressed multi-family property (using my own savings to supplement the down payment)- BRRRR that multi-family property and keep repeating from there Here are my questions:1) Would I be better off forgoing the two SFHs altogether, and continuing to rent an apartment until I have enough money saved up to buy a multi-family property as my first investment? 

Hello,I had a tenant last winter and the heat in his unit was supplemented by the unit above him.It gets really cold down there in winter but he chose not to have free heat and sealed the vents tightly with an aluminum foil without  letting me know , I could have easily adjusted the thermostat to lower  per his needs if he had told me and supplemented my apartment above with any additional heat but he chose to seal without letting me know inspite of my warning later on and obviously it can have detrimental effect on the tubing inside the walls due to excess pressure build up.He also complained about high electricity Bill's (obviously he would incur high utility bills when he turns on his electric radiator without using the free heat he was getting) I ended up having an oversight from my end as I did not verify if sealing vent caused any damage . 

Fannie Mae loves there is this opportunity for the borrower to supplement their ability to repay the mortgage.

I was never looking for something to jettison my day job, which I like, just something that worked good as an investment and would supplement my pension.

or are you happy with a few rentals for supplemental income? 

I was planning to supplement my income with other freelance or part time work while working toward buying my first property.However, I just received word from a lender at a credit union that they won't count income from a part time W-2 position unless I've had it for at least two years.

I also notice that my clients that do this are older folks, and just need supplemental income for their retirement.