A lot of what I do simultaneously hardens the rental too, so it's a dual benefit.  

I have simultaneously seen many people consistently put substantial money down and slowly build multimillion dollar portfolios over the course of 3-4 decades with little concern for whether times were good or bad.

All 3 must work simultaneously, or they really don't work well...or at all. 

And to further the conversation on the due on sale, is creating a trust using the sellers surname and then having the seller transfer title to the trust, and then purchasing the trust simultaneous to your closing a viable option to navigate away from a due on sale loan call?

My plan is the renters would be able to cover the mortgage, utilities and HELOC cost and I would be able to basically use that money to start building equity in a new home while simultaneously paying down my current home.

If you can buy 1 or 2 houses simultaneously, DO IT.  

Here are a few general steps using traditional commercial loan financing: 1) At a minimum get Rent Roll and T12 from Seller; 2) Submit an LOI to the seller and agree on terms; 3) Get attorney to draft a Purchase and Sale Agreement; 4) Seller agrees to terms in PSA; 5) Look over all property documentation PRIOR to due diligence period starting; 6) (Simultaneous with other steps) - Appraisal/Get loan commitment from lender; 7) Inspect Property...Best way to finance deals is the way it best fits your investment strategy, goals, and desired returns. 

I was a real estate investor/developer/flipper/holder first, then became a contractor and I run two businesses simultaneously.

You cannot have 2 FHA loans simultaneously, except for a very limited number of exceptions such as job transfer 100+ miles away, maybe a change in family size, etc. 

I was able to get approved for a Cash out refinance while simultaneously dropping my mortgage 15 years and a percent and a half. however after speaking with my new lender and them letting me know how it was a little bit harder to get me approved this has me worried about getting approved for a second mortgage.