It's a good idea to search for an optimal market in which to invest, one with cashflow favorable economics (population growth, wage growth, employment growth etc) and a balance between supply and demand.

Whether that is ‘optimal’ idk.If you lower your cost of living enough it’s definitely possible to retire early on indexes via the ‘safe withdrawal rate’.

Of course I'm busier day to day when I'm actively buying and then renovating, but once the property is stablished (optimized for highest and best use with tenants in place), then I'm back to the slower zone and that is when I travel.

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.