But this type of investing becomes geometrically more risky as you near the end of your career. 

To me, getting started is risky enough. 

Also, I am a little nervous about it being an election year and the effect this can have on the market, so I am wondering if its risky buying in the midwest.I plan on holding on to these properties and I feel like I can wether a storm, should it occur, however buying high and waiting for it to go back up doesn't sound exciting.

I used to think it was risky to tell people but I believe you have to hold yourself accountable if you make your goals transparent. 

Ch. 1 Why I Love Rental Properties Ability to use the leverage Ability to hustle for greater returns Ability to manage my investment directly People always need a place to live Its worked for millions of people before me Fairly stable and predictable for those interested in long term gains Not having to be presentThe 4 Wealth Generators (from a rental) Appreciation- natural and forced (the only generator flippers get) Can be very risky but can be the icing on the cake Cash Flow- buy properties that offer cash flow today.

@Michael Heisterkamp I mean his numbers here aren't insanely off the reservation, he's not accounting for any FML moments, but beyond that I just think he's organizing the acquisition and finance structure in a way that's way more risky than is needed for same-ish results, given the scenario he's running.

Another risk is that a tenant goes on a winter vacation, boiler goes out and then one of your units doesn't have heat for a week or two.

Holding the property and letting values increase seems risky both because of the sheer law of averages on our market curve, and also due to the limiting factors of our high taxes.I have to confess that I spent a long time in the HELOC zone.  

It's extremely risky for the lender to be at that high of an LTV with a borrower that hasn't shown financial responsibility (low FICO).

That was a huge mindset shift for me... that by taking action, I'm actually doing the LESS risky thing.