However if you understand the process already and what you're trying to achieve and just looking for someone to do it for you, then I would search a bit more to price compare and then make your informed decision.

Were you making a calculated decision?

It can make leasing a bit harder since you will have more vacancy when those come do but it will all be in peak season.With respect to the hiring decision, you would need to hire someone to replace you (perform the same functions you currently perform) so that you continue to work up the ladder (spending more time on higher value tasks).  

Is this a wise decision to use a HELOC on property number one that only has 20 to 25% equity in it to fund a down payment for a live in house hack in multifamily property number two?

No one right decision for everyone. 

I think my main pain point is underwriting the property as it is and then seeing what it could be and then making decisions on if it's worth and how those decisions are made.  

Their decision to expand into Ohio is not just a strategic move for the company but a significant boon for the local economy.

I would encourage you to do a deeper dig on the financials and take your own skill inventory in making this important wealth impacting decision.  

I know the decision shouldn't be made of tax benefit alone but starting to think other areas may help me accomplish both more efficiently.

There are so many "easy" decisions when you form an LLC that aren't really easy, and you need a good CPA to see your entire situation before they can give you good advice.