The plan is to sell primary residence in order to have the equity in cash and utilize that cash to fund the multi family purchase and have operating capital. 

I do have funds saved for investment purposes and equity for a HELOC in my primary.

Planning ahead can be challenging when two nearly identical loans get UW and conditioned in very different ways at the same lender.  

Very very different tenants, costs to operate and jurisdictional issues. 

We have 2 W2s( Me+ Spouse).Have a primary residence SFH and 2 rentals.I have around $40K of rental income after all the deductions/depreciation.This time I used a CPA and I am a sure he tried his best to get all deductions possible.

My intention is to become a small but mighty Real Estate Investor.My primary market would be Florida but I am open to relocation later this year if the right opportunity presents itself elsewhere.Looking forward to learning alongside you all and hopefully connecting with many of you as well. 

Also, if I compare different lenders, if we just compare rate, for the same rate, less point is better, right?

Make that property their primary residence.  

We are seriously considering this to decrease inheritance tax as shares in a property are considered differently in RI for inheritance.

This is why you can have two similar buildings with different tax bills.