If you put a school in this area I can see a great deal of teenage driven businesses moving there which will change the atmosphere of Mass Ave completely.

Well, unexpectedly, that area had prices driven up by oil worker demand for rentals. 

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).

Almost every potential flip on MLS gets a bidding war and the price gets driven up to where its not worth buying it.

I've driven back and forth from Rockville to Frederick at least 10 times in the past 2 weeks.

Tenant of Unit A is leaving, so i intend on renovating with recarpeting and new paint and leaseing it out.

A) I am not a lawyer, and this is not legal advice.

as a flipper and broker in WI (marketing my 20th flip) the best deals rarely come from MLS in Hot and heating up markets, cuz every Tom Dick and Harry comes out of the woodwork with no idea where else to look, they say, "hey we should flip a house, like on TV" so the easy ones get driven up in price, and your margins driven down. that being said, I have flipped listed properties, (6 i think) and have made ok margins, but the ones that were fantastic were acquired through other means.

At present, the value and assessment of the units is driven down by condition.

I'm leaning toward finding a smaller principal broker who also manages property versus a large, sales driven firm.