What is the best way to separate my finances in your experience -my gf and I will be looking money together to buy another property together to take advantage of her first time homebuyer status.

I will be taking full advantage of these.

Again the goal is to take advantage of accelerated depreciation for this year. 

Are their tax advantages to financing as a conventional rental property with 20% down vs a vacation home with 10% down? 

Knowing that the value will eventually go down when the market settles down, I want to take advantage of the equity while I have it!

The advantage here is that I will have most of my capital invested in real estate, which I believe has higher returns than the stock market.

So it makes sense to take the depreciation.You may want to seek the advice of a chartered accountant in Canada and a CPA in the US to make sure you are taking advantage of all of the benefits available to you.

Take advantage of your situation and crawl before you walk.

The tax advantages, the cash flow, the principal pay down will all continue if you keep the property.

Hopefully you can take advantage of some 100% bonus depreciation to get a nice offset for your 2021 taxes.2.