I will definitely have an inspection contingency on it just in case there are massive problems I'm not expecting.  

I thought about Pueblo also, but again, nothing to good down there either, that didn't need massive rehabing.

.- 3-4 units still puts you in the residential category- 5 or more units is commercial residential and most lenders will expect you to have experience and will generally have more restrictions on the lending process- A 10+ cap rate in the Boston area will be extremely challenging to find unless you are planning on a massive value add or redevelopment- No idea what your personal financial situation, but a 3 family in Worcester versus a 20 unit requires a very different upfront financial commitment.

It may also be possible the other development that happened in Kenosha County is finally reaching Racine.I own rental properties in Janesville (probably 2 hours west of Racine) the city is doing a massive reassessment this year.

I will say there's plenty of catalysts out there; Stretched labor market, high corporate debt, overvalued assets, massive government debt on almost all levels, geopolitical instability, failing pension funds, political uncertainty, and on it goes.

In the same way, areas like North Nashville and Old Hickory are seeing massive profits on the flipping side.

I don't want to talk about massive cities that were once prominent in there respective states such as Detroit or St.

Other than the massive paperwork you might not know where you stand for 60 days. 

Your other point about the counter offer, i think you should keep a few things in mind:  Montreal is in a massive seller's market right now.

I cant see a garage conversion being massively out of code unless they've done structural changes (load-bearing walls, which would be exterior anyways).