Also, if you have other sources, like a 401k loan, to supplement the cost, you can make this work, as long as you can cover your mortgage payment with the rent, I would keep it.

I think the big question for me, is your ROI enough to supplement what you would have in the 401k at retirement time?

My goal is to acquire cash flowing properties as a way to supplement my primary career in corporate finance (FP&A).

I am just a College biology professor who is now a small-time RE investor to supplement my meager teacher's pension.

I never looked to the Future for Retirement I was mostly concerned with just riding my motorcycles going to work to pay some bills and just ride like I have been doing for over 35yrs.Well that almost came to an end last year when someone decided to run a Red Light Late I T-Boned a Truck on my motorcycle on my way to work and am lucky to be alive to type today.To make a long story short I am getting a Settlement enough to buy a home cash if I want but looking to invest in Rental property to help supplement Retirement.

Commuting seems much less likely from the west side of the river, but the second home buying crowd definitely still supplements the local buyers pool, depending on the area. 

Are you prepared to supplement the cost of these units until rent appreciation results in positive cash flow? 

Over the last 4 years I have supplemented my income by buying and remodeling 8 run down homes and selling them.

I'm considering the possibility of getting a license at some point to potentially supplement the education and experience here and through self teaching on how the whole process works.

Assumption buyers can often get a supplemental (think: second mortgage) but those carry higher rates so the buyer still needs a discount.