I've toyed with the idea of getting into small commercial, but for reasons mentioned above have never pulled the trigger.

Only a couple have pulled the trigger on those so far, but it seems like a decent thesis.A lot of them have continued to buy high end homes for STRs as well.

Come December, I was ready to pull the trigger because Ashley has just acquired her newly minted real estate license and joined the FI Team, and by the time I would close on this property, 12 months would have elapsed since I last purchased a primary residence.Thanks to Ashley and her expert negotiating skills, despite this being her first deal as an agent, we were able to get this property under contract for $10,000 under asking at $665,000.

I had read book after book after book... listened to virtually every "Real Estate Guys Radio Podcast".... watched Income Property... took real estate courses.... etc... and never got to the point where I was confident enough to pull the trigger. 

Between being in the military and not having a solid plan after 5 years passed without me pulling the Real Estate trigger. 

In the meantime, I spoke to real estate professionals in the area of these prospective properties, to get a better idea of any potential intangibles that I may not have been able to glean from the internet or having lived in the area(s) personally.The professional experience and (cross verified) area knowledge that they provided, fortified the months of researching/understanding needed to feel comfortable enough to pull the trigger.

I am so ready to get started but, like many others, I find it very hard to pull the trigger when properties are at such insane prices.

I can't even get close friends of mine to pull the trigger when an opportunity arises so dealing with complete strangers is going to be difficult but that's why we're all here right.

All I am saying is be very careful and make sure you run worst case and best case scenarios before you pull the trigger.

Canned messages work better IMO through Airbnb; they recently introduced scheduled messages based on a few triggers like a confirmed booking, check-in, and check-out.