Fortunately my mistakes never did cost me 'too much' (relative term compared to how bad it could have been).  

I am a "Millennial" looking to invest in rental real estate and every time I talk to someone my age about my real estate investing goals they look at me like I'm insane!

You earn what amounts to 2.22% cash back on any purchase, that can be redeemed against any travel-related expense on your statement (anything from an airline ticket to an Uber ride).  

The side job has to be RE related.

Foremost typically offers a relatively reasonably priced policy and you only pay as you go vs being a "fully earned" premium. 

Today on The BiggerPockets Podcast, we sit down with Bryce Stewart, a former school teacher who was able to quit his job at age 35 through the smart purchases of small multifamily properties.

When buying a $100k property in those markets your risk should be relatively low as again you are hitting the higher end of rental price points.

I just came across this article from Calculated Risk (the article is about a year old so here is the latest data.) which suggests that MF demand will start to shrink due to increased supply from new building and decreased demand from those aged 25-39, who will make up the top three age brackets in 2020, who will enter their prime home buying years. 

My other concern is cap rates are relatively low between 6% and 8% max (cash on cash). 

Do you not have any relatives, friends, or reliable handyman nearby that would either handle it or contact you?