It is hard to stay calm and always be hospitable when dealing with guests in so many different situations.

With your background in lease management and site selection, that could be a natural next step.Regarding STRs, I can understand the hesitation—accurate expense tracking is critical, and not having that data can make evaluating deals frustrating.

If it is a direct lender you are able to work to find more favorable terms because they usually determine their terms on a deal by deal basis. 

To maintain control and avoid being locked into larger deals, consider directly owning replacement properties or exploring a partial 1031 exchange while carefully structuring syndication investments.This post does not create a CPA-Client relationship.

However, we just started STR property management and it would be very helpful/look more professional to have the ability to esign contracts, autogenerate payout statements, direct deposit payouts, ect.  

For a variety of reasons, including keeping this potential project "need-to-know" only right now, I want to get a ballpark estimate with full understanding that the goal posts could move in either direction as the project gets more discrete. 

Then I would either go to your GC with the info, or go directly to your subs (licensed electrician etc.) with the info.

There are deals now.

My area for example has to have certain signage and an emergency shut off button located directly by the hot tub. 

I have brokered several deals in the Cleveland market.