While selling in Rochester and investing in states closer to Chicago would still require finding a reliable PM and likely making improvements, the advantage is that these new investments would be in a market that I can occasionally drive to.

I am considering taking out a HELOC on this property to purchase another property closer to my primary residence.

I spared some details but its closer to me than just "a seller". 

As you will deal with every horrible thing in life.... tenants disputes, sleazy contractors, the city who hates your grass, everyone has a sob story and can't pay rent, be emotional ready for evictions and threats, and know your lease and local laws.

If you want it to be a distressed/motivated sellers, it needs to be closer to 200-300 people, maybe more in some markets.2) That's why lists like those already mentioned are important.

My first suggestion is to only look out of state after you have "cut your teeth" closer to home where you can experience and learn from the process way more quickly. 

That was the case, but the MSA is closer to 3.5 now.

I'd build on an infill lot closer to downtown. you can get land within the downtown markets and construct multifamily properties through the same process and higher units and better floorplans. we just passed our first triplex in central ohio and are breaking ground in 3 weeks. 

They ask us to step in for everything from a lightbulb to grass seed to whatever.

As it gets closer to death, it's increasingly likely that it will have more accidents.2.