States like CA, NY, CT, NJ, MD are notorious for high sale price homes, higher taxes and hard to cash flow.

Tax structures and mortgage regulations might also shift as canada mortgages are very different.What do you think would happen? 

If you're going to make a lot of changes, I recommend consulting an attorney to ensure you're updated on the laws.

I'd definitely consult an RE attorney who is versed with dealing with these. 

People are going to start thinking about spending their tax refunds in the middle of January.

However, I do not know who this could be beyond a property manager which would not work in my case since I am looking to self manage for both tax (material participation in STR loophole) and profitability reasons. 

Taxable income is not cash flow.There are a myriad possibilities for taxes.

Here are the pros as i see it: easy (no purchase necessary, you know the property), likely prop 13 property tax discount, possibly below current rate loan.  

Also, we'll need to know what your other expenses will be (taxes, insurance, etc.). 

After this tax year, I will know exactly what I need to do to progress.