Feel free to reach out, Im only licensed in HI and WA state (so not trying to steer you to any company) but I'm always happy to help out fellow veterans/answer any questions you might have. 

In Washington we have similiar laws.

Our goal is to convert it back to a 3-4 unit property for long-term and short-term rentals.As I currently reside in Washington DC, I'm unfamiliar with the local permit processes and requirements.

@Paul Washington I've heard of other investors doing it.

I happened to be looking at Monday's houses briefly only because a friend asked me to comp one property's value for him (because I've got mls access as a broker and he just wanted a quickie comp) but I stopped there so I don't know about this one in Shorewood you mentioned.As far as the suburban counties, as you may have noticed, the more well off parts of MKE Cty aren't very well represented compared to the less well off areas, so when you look at the other counties (like the Waukesha Cty sheriff has a running listing of the next maybe 5 or 6 weeks of auctions on their website and each week there's usually 10 to 20 TOTAL each week and quite a few will be in the relatively few not so well off areas of the county and you'll be hard pressed to find many in Chenequa, the most expensive community in all of SE WI) Ozaukee has very few as well as Washington County and I'd guess its the same pattern there as well, but you'll have investors in all of these counties who are watching them. 

In our state (Washington) you must send the lease non renewals 60 days in advance and they have to be served (posted at house and mailed).

The top area choices for 2-4 unit multifamily investors have been:Valley Stream & Port Washington: 14 deals, respectivelyLong Beach: 11 dealsLynbrook: 9 dealsSuffolk CountyLike the Bronx, Suffolk, too, saw a 43% increase in 2-4 family inventory.

In our state (WA) the tenant is responsible for pest control (as long as it was pest free when you delivered it) for SFR and the landlord is responsible for multifamily.

In the future, if the only red flag is a house fire and hotel situation, you can always make a public records request on the former address at your police and/or public safety administration in your city/county.

. ;-)  well working south side of Chicago  south jackson MS  Baltimore city  Philly west side I understand the risks .. and I am with my clients who are armed most of the time and when i started buying this stuff it was south of 8 mile in Detroit.. so understand that risk.when I bought courthouse steps in the PNW  Portland SW washington no so much worry about armed folks although that has probably changed with the housesless folks / squatters these days.