Any taxes or other issues that I may run into down the line?

As most investors seek to do in real estate, we want to generate positive passive income through multiple avenues such as equity, cash flow, and even tax advantages.  

My question is this, can I deduct my passive losses that occurred in 2017 on my 2017 taxes or does it get rolled over to 2018 because my income is too high?

The very basics would be getting your furniture and shopping list together, keyless entry like Schlage (with backup lockbox with physical key very close as well), looking into insurance, local taxes for STRs, and moreAlot of ways to save time and make it easier to self manage with a property management software like Hospitable and data research like AirDNA.

Or stay a second year and sell tax free. 

If the rate is reasonable then it may make sense to try to save fast to get to the 3.5% down payment on a double or triple - househacking may allow you to increase your savings rate and pay down that loan even faster.As for estimating costs, closing in NY factor at least 1% of the mortgage amount for tax, plus $1500-2000 for lawyer, title and fees, then the amount required by the bank for escrow will depend on the actual property taxes and insurance.

I know how much my property taxes will be, but what other expenses are there, and approximate cost? 

Have a good CPA to help come tax time. 

My property tax increases have been 17% for both homes (no Proposition 13 like in CA with our max of 2% increase).  

Double taxation would be when you have to pay US income tax and then also Canada income tax and you don't receive a credit for your US income taxes.