But for any sort of regular support its a really pain unless the agent has a "buddy" who can quickly look everything up and somehow help with access. 

I've had foundation repair recently due to the extreme heat over the summer, neighbors are friendly in my area and also help with monitoring my short term rental.

I regularly track those percentages much like I track the breakout of my stock market investments (Growth, Growth and Income, Aggressive, and International (Yes, that’s another Dave Ramsey’ism).

IF so, your property management company should be able to quote the work, and monitor it. 

Hand written letters work well when you deal with regular home sellers that are looking for just a one time buyer to buy their house.So what I would do, is don't hide the fact that you are a company, show it off.

When you sell make sure you look into a 1031X rather than a regular sale so you can defer the taxes. 

I'd like to set up a meeting on a regular basis to form some community, share what we're up to, and synergize.  

The regular way is not working.How do people pay their contractors from long distance?   

We have an app that we now use to remotely monitor water usage for bill back purposes.

Bigger Pockets has some great state forums and usually there are good locals that monitor those.