Given that, how can I take advantage from a tax perspective of losses on passive activity from owning rental properties?

@Maxton JohnsonIt really depends on what real estate activity you are trying to be involved in.It also depends on what your goals are.It is true that for a NY LLC to be established that it needs to have its information placed in 2 ads for 6 weeks.

Years ago I did some work with SaskTel downtown and there use to be a pretty good Japanese restaurant just down the street (not something I expected in the middle of the prairie).Looking at what you have posted - and with the caveat that I do not know the market in Regina {property taxes must be low} - my first question is does your figure of $1445/month include: snow removal, lawn care, maintenance reserve (~10% EGR ... which is more like $5500/yr) and property management (say 7-8%)?  

Since you'd prefer to be MLS only vs. an active realtor your broker might require some compensation too.

I have been looking for a decent house in a decent location for 3 months, I saw like 10 houses (price range 200k-380k), and most were in terrible conditions or in good condition but next to superloud 4-lane streets.

There are applications that will use the Google Street View so you don't have to physically photograph houses...

These houses were built by a company and are all on its own private street and pretty much identical to each other.  

I actively invest and sell real estate in Pensacola and I think it’s a great town for buy and hold.  

We don't want to through them on the street, they are really nice and decent people.

Local banks are generally more useful once you have to many active mortgages to get a loan from a major bank.