I then have my Chase Business Account linked to Stessa so it will import the payments and still run all the features that I like (Tracking Rental Income, P/L statements, Tax form simple print outs) because it will sync with my Chase Business account.

A $200,000 duplex might have identical rents in municipality “A” and municipality “B” but the property tax rates will vary, local regulations will dictate licensing requirements, labor rates will vary &  the particular location will dictate insurance premiums since insurance carriers will weigh local replacement costs and whether the municipality is viewed as being a “plaintiff friendly” in arriving at insurance premiums.Better situated assets will attract better tenants.

Taxes are a certainty regardless of where anyone stands financially, so the yield return of investment referring to the capital gain received will be taxed.

Have you run the numbers including property taxes and insurance?

All in all its a good time in many states to make the move and NY does have several cities where the taxes and home prices are not that bad outside of the city.

In my area, lenders want to see a tax return, minimum of 1 year of rental income history before counting that as additional income.

Keep in mind that the taxes becoming uncapped will have a large effect on your numbers if the property was purchased previously at a much lower price. 

You could do Florida, but you'll navigate the HOI issues which have run crazy.My suggestion would be the outskirts of Nashville; no income tax, okay property tax, growing, pretty centrally located, etc. 

I'm not exactly sure what contracts need to be signed and I'm looking to source one, this is something I'm currently researching further4.1) The contract needs to protect me from seller's bankruptcy, change on mind for the deal, assist me with the lender in the future if required and more5) Inspect the property, check for outstanding lien, hoa, mortgage payment, insurance, tax 5) Closing costs - agent 2.5% ( if they are part of it ), escrow/title transfer (??

You can pay extra for the bells and whistles but you can store all the lease info and it will make taxes much easier.