Nice folks and a lot of knowledge to go around. 

I've worked with some Canadians buying  here in Ohio.Indeed, rather than selling your stocks to fund investments (and lose out on any potential price appreciation and dividend payments, as well as incurring capital gains taxes), a nice alternative is to borrow against some percentage of the holdings.You would start with the brokerage where you hold the stocks and see what their loan program looks like for the account you hold. 

October is a popular conference month since the weather is usually nice in most places (including Vegas!)

I live in CA and drove that route for years to visit family in Phoenix, AZ. 

So, I think you have a risk factor in upstate New York that you don't get in most other areas (it's not where most people would choose to live).I think upstate New York one of the few areas in the country you can cash flow in B areas with 80% downpayment, so that's nice--in terms of deals, I think the numbers still work out at market prices.Finally, the property taxes are very high in upstate New York. 

I have two local rentals that cash flow nicely, but all that profit is thrown towards this house so I'm completely negative. 

A nice but expensive duplex on a beach or in an expensive area might be ideal, if you can swing the other half out of personal funds. 

Cash flow is nice and definitely important but true wealth is built in equity.

You can look back in a short time and see a very nice portfolio.  

From personal experience, there are multiple issues that can pop up and it is nice to be local to deal with them.