Our current tech stack is a mix of Buildium (very clunky), Breezeway (great, but limited without a PMS), Xero and Google Suite tools with lots of spreadsheets involved.

I work on projects across multiple states and have a strong network of contractors.Regarding when to involve a contractor, if it’s someone you haven’t worked with before, I’d suggest waiting until after the inspection.

The Chicago Association of Realtors'® specifically state "When you become a Dual Agent, you owe equal fiduciary duties at that point to both parties in the transaction, and you lose the ability to negotiate for, strategize and advise either one."

I also had horrific PMs, particularly involved with a 48 unit apartment complex in Houston.  

It isn't having paid off properties that offers security, there are still taxes, insurance, maintenance and management involved. 

Turnkey properties offer immediate rental income with less hands-on involvement, while properties in need of rehabilitation can potentially appreciate in value.

There is still some paperwork involved but significantly less than traditional lending institutions.  

REIA's, BP Meet Up's, General Cow Tipping Parties?

We act as GC on our efforts but we have gotten tired of the effort involved.  

Usually conservation easements come with Huge tax benefits for the party putting the property into a CE.