The operating expenses above though look awfully low for the year, almost as if vacancy, maint and Capex savings aren't accounted for.Can anyone help set me straight... or is this actually a bad property (at its current list price)?

Seems like prices are low for property and taxes (a lot better then NY).

The operating expenses above though look awfully low for the year, almost as if vacancy, maint and Capex savings aren't accounted for.Can anyone help set me straight... or is this actually a bad property (at its current list price)?

Is there a thing as offering too low in real estate ?

It is also to make sure I catch any problems early and fix them at low cost. 

I think house hacking is a great way to get started investing and you could probably get started sooner than you think with some of the low down payment programs available today. 

So $3,900 - $900 - $500 = $2,500 with low occupancy at a slower season.

I know Windsor is more affordable in general, but i'd assume it also means low rental income. 

You make your money when you buy, so you want to buy low enough to have enough margin to cover rehab plus your profit at the end.

Buy low sell high.