I've gotten county data before that I honestly could not scrub down because it was that confusing, and I've developed and coded my own highly automated CRM, so I'm not exactly tech-illiterate haha.  

This process can be automated.

Again, if you have an assistant with a $20 hourly rate it could be worth the manual process.I'd be down for automation though if there was a solution that provided it.

Those services are more for automated showing (through lockboxes) than inspections. 

I want something more like an automated database than a spreadsheet that enables me to do quick drive-by estimates so I can deliver an offer "subject to", and then expand it when I get back to the office into a more thorough analysis, should I get a response from the owner.

Just need to focus on setting up your systems to automate things.

If I had numerous STRs, I would be looking for a way to automate the PIN establishment with the guest.

As I am an out-of-state investor, automating that is essential for me. 

Also, what work are you good at and what do you want to outsource/automate? 

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