Chicago is a lower appreciation market but with the trends we've been seeing with increased rates of hurricanes on the east coast and fires in the west, I do think long-term we will see some migration to the Midwest.

You haven't seen it, but you know automatically that that you can increase the rent by $25K a year?   

When the ROE is significantly smaller than my CoC return (based on initial investment) I know it's time to make a move to increase the velocity of the money.

I am proficient in investing and confident in earning 7-10% returns in the market over the next decade or two.

So if there are any issues, I'll see those upfront and can adjust my plan as needed.He has already mentioned he's ok with me removing the tenant or raising prices if necessary.See my other comment regarding Deal Calculator change and maybe presenting an schedule rent increase option for the current tenant.

We’re looking to increase our lifestyle through the decrease in housing and built a little passive income medium term. 

The market between the 2 locations & resident class (Especially if you plan to self mange or find a PM company), Your future goals and the costs associated with moving and transferring to a new hospital. 

The shorter the prepayment term has an impact on increasing the rate.4.

There may some merits to investing upstate/western NY, but I would suggest doing some serious homework into eviction timelines, annual rent % increases, etc. 

In the past two years we have completed over a dozen flips, We are holding 20 rental units self managed and 2 self managed Air BnBs.