Would these skeletons in the closet scare you away?

[Rochelle Thea Fabrizio]

I am Active Duty military and moving to Great Lakes this coming summer. I have been keeping a very close eye on the market for several months already with little luck finding the home that suites ALL of my needs. I have somewhat of a strange situation as I purchase a house at every duty station, however I was interested in house hacking or purchasing a multi-unit property this time around as well. (I currently own two homes that I rent) I finally found a home that seems to tick all of my boxes #1 home size (2,240 sqft main home 1,100 sqft back home) #2 Lot Size (1 acre total with 0.35 acres of it for back home) #3 Commute #4 School Districts #5 Already established rental income. With that being said this property has some weird circumstances that are going to be affecting it very soon and I am wondering what your intellectual insight would be. 

#1 The road where the property currently resides is getting enlarged. They are taking 10 feet of property initially for construction and than returning 7 feet after construction is complete to leave a total of 3 feet taken. After speaking with the agent the WisDOT is not 100% finalized but the compensation is going to the current resident (even though he is listing it at the current lot size not the reduced lot size and will not be the one dealing with the undertaking and loss of property)

#2 There is also a significant potential to add a road from the city just South of the parcel. "If" this road were to be built I will be required to move driveways (2 of them) to that roads location and remove them from the other main road being expanded. 

#3 If the road described in problem #2 is installed with sewer access, the back home which is currently on Septic will be required to be converted to City Sewer at my cost. 

#4 the house is currently in a location zoned SFR and is non-conformant but "grand-fathered" in to this exception. I am being told in case of something happened I will not be allowed to rebuild one of the homes.

I would be living in the bottom portion of the two homes for a little while with the upstairs 2Bd/1Ba unit being rented at $450 and the back home at 2Bd/1Ba being rented at $550. Both units are below market rent. That would leave my monthly expense at approximately $700 (with current rent) which for me is very, very cheap. How worried would you be about the above mentioned situations and what would be your considerations? Thank you all in advance for you help!