(conservatively underwritten)2) Could we find (and afford) a stronger performing asset with a reasonable amount of focus and hustle?

How good is the earnest money deposit (a higher deposit generally signals stronger commitment by the buyer, minimal deposit could mean--meh, I could take it or leave it). 

Community aspects, are you a contributor or a taker, do you add to a stronger neighborhood fabric, do you positively influence property values of other owners, or are you detracting from it?

Demand will be stronger imo however in the burbs.

If you are going to move out of state, I would definitely sell and buy something that has stronger cash flow.

That is not bad for appreciation, especially combined with the still low price tags compared to many of the costal markets.According to 2016 GMAR data Milwaukee County is up 11% (driven by hot markets along the North Shore area like Shorewood, Glendale, Brown Deer etc who made up for the lower performing areas) the markets in Ozaukee County show even stronger appreciation with +13% ( driven by Mequon, Thiensville, Grafton, Cedarburg etc).

There are quite a few out there, and a lot that are in way stronger growth markets than Ohio!

Find the hidden jewel property that others overlooked because it's not the sexy option, or look at out of state markets that are stronger (like Utah).

As the market has gotten stronger, more people are flipping.

Your money could work stronger in some other deal.