Knowing more specifics about your scenario and goal, will help provide a more customize approach for you. 

But you can customize any policy to make the premium lower.

My next goal would be to invest in out of state short term rentals and add those to the portfolio, but not sure how that would impact my LLC if I create a Wyoming Trust/Holding Company/LLCs and foreign file for incorporation into Connecticut to complete the first deal for the duplex, but then what happens when I want to invest in out of state investments deals/opportunities/homes? 

Not every customer service situation runs smoothly, or obtains the hoped for results.  

Customer service is very helpful as well.

When is the best time to start incorporating these professionals during the journey? 

You simply pick a name and create your articles of incorporation it will provide you with an EIN number go to your bank of choice and open up a business checking account.I live in Florida and have created multiple LLC's on that site in minutes. 

Another point that I forgot to note, this will be a sales director position covering the midland area and surrounding regions, so I will be frequently traveling to midland for customer meetings and team meetings (2 times per month typically)! 

We've seen thousands of posts where people are looking to get out of their job and away from people, bosses, and customers and want real estate to be that way out. 

I've learned the hard way that potential customers don't like to hear the word, "NO"!