For new lease signings (not renewals), if being signed electronically I will often do a video conference with them and review the lease in detail so that they understand it and can ask questions before signing it.

Go to some conferences, sales training etc.

The Inman news conferences have been great places to get outside of industry groupthink.

You can also attend conferences in person to meet other investors and explore mentorship options.My brothers and I actually found our current mentorship program here on Biggerpockets!

I'll try to stay away from being political here - but if the city has a left of center political reputation and management / leadership style.

Most of our tenants come through Sabbatical Homes.We have detailed walk-through videos of both of our units (and We also provide video conference calls with prospective tenants. 

But as you said, it is going to be late 2020's before the first ticket to ride is issued and it would take some deep pockets to implement a buy and hold strategy to go after high density multi-family, conference, or hotel development.

In my mind I feel like you need an LLC or business to be able to write items off no (thinking depreciation, property management, any tools used like Stessa/Rentredi, or classes/conferences paid for as education).

This was a big focus of the STR Wealth Conference, was having your own booking site and building your brand (for your property).

(this is a MUST) In any market - as long as they agree with the underwriting and have confidence in your leadership.