With current interest rates, and they are at least 1% higher with potentially additional points for non owner occupied property, it is hard to find properties that will allow for positive cash flow after paying the mortgage, if you are looking for money for the down payment from a private lender, those are normally at higher than market and I am not sure it would be possible to pay it off.... please remember you need to take into account that you may not have a tenant for a certain amount of time, a tenant may stop paying rent, or you will have a big ticket item to fix, so I would wait if I were you and save to have enough for the down payment and closing costs and perhaps some money set aside for repairs. you also want to make sure that you have your own emergency fund outside of the money needed for the investment property because life happens ....

Do you think this strategy gains strength if lets say... in five years interest rates are at 5.5 vs 7.5 now?  

Taxes will still be owed on the boot plus depreciation recapture (approximately $105K taxed at a 25% rate).

Shoot me a DM if you want some help with finding a condo or house with a low rate that's on market.

Comps do not lie, if she pulled similar ones then that's what it is but if the agent did not take into account the bedroom and lot size that would change the value.

This would allow you to maximize tax deductions at ordinary tax rates.

My main concern is the interest rates being so high now as to whether what I'm hoping to achieve is really even possible. 

Sad that NY isn't taking advantage of expensive hotels to get most of the US traffick to stay on US side and just do a day visit to Canada side and come back.I don't know why small towns change their STR rules and make restrictions.

However, value add with a sale is not as implacted by rates.  

But the fires have changed things.