Specifically, I'm curious about how you find information on local regulations, how you automate the process, and how you make it fast and efficient.So far, my approach has been to call each municipal building to ask about their regulations on short term rentals.

Denis,Yes, but keep in mind some lenders have specific overlays and will not allow. 

Our rental is paid for and has rental income of $2200 month and our primary has a mortgage of $1800 so we are currently living for free basically.we have a credit line on our rental for $275k and recently got a letter from our mortgage company offering a cash out refi on our primary of approx $300k and still be able to keep our current interest rate on the remaining balance of the mortgage which is mid 3 %.We are trying to grow our rentals and struggling to figure out the best way to do that.

Structure your offer to make it the most beneficial for you as the purchaser.

Offer some incentives like paying for their move or covering the security deposit and first months rent at their new place.

We in our SEC offering listed real estate as one of the safest and they came back to us and said to prove it.

Look at the existing inventory in you're area, find an investor agent who has experience with house hacking, pick the best option currently on the market that fits your budget and make the offer. 

The market is quite competitive, most offers are over list price.

I know this is a learning process, so I would like to know if there is anyone in the Section 8 investor realm that could offer advise and what they did when they started? 

Specifically, that husband and wife could each own their separate primary residence.