I think a good property manager should be able to suggest the optimal rate for rent on that area.  

I get optimizing, but chasing what in the long term amount to marginally increased returns doesn’t make a lot of sense to me, especially when the down side is capital loss and the potential of delaying your purchases, which impacts the main wealth generators of RE, cash flow, amortization, appreciation, and tax savings.

Driving operational excellence and optimization within the logistics, operations, supply chain and distribution area through leadership and innovation.I have have been investing in real state since 2002.  

A good CPA is able to help investors find the optimal structure for their business and transactions to work for their goals and minimize taxes.

For most, the answer is not binary (keep or sell the HQ) or immediate...the answer lies in between where less space is needed for the same workforce, or the same space will be used as the workforce grows.COVID (and technology) has exposed leaders to possibilities...and accelerated the evolution of flexible work plans and facilities optimization.

When is the optimal time to secure and attorney?

What one should be trying to do with a portfolio is optimize the risk/return given their resources.  

Not ideal (to put it mildly).So long as you aren't forced to sell, hopefully the area will grow to justify your optimism. 

This is a guaranteed return compared to investing, but obviously not the most optimal as we could potentially get much better returns in Real Estate.

It seems like the premium market is not optimal from a rental standpoint.