I would use a service such as vacationrentaldesk.com for this.A direct booking is no more risky than a booking through VRBO or Airbnb; they aren’t verifying identity, either.In fact, my own company has taken thousands of reservations over 19 years, and we don’t verify identity.  

I sold it for way higher than I bought it.

If we can cut that timeline down by a couple of years that would be preferrable...

I quit my job in tech a couple of months ago and I'm excited to pivot into real estate investing. 

It's usually more expensive than a mortgage.

As long as the total of whatever you purchase is equal to or greater than the net sale of your old property you'll defer all tax.  

So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

The past couple years they have been tightening up on giving permits for STRs but this year they have the jubilee happening so they haven’t been as hard on it but that could easily change after especially with the move Spain just recently announced and Venice and Florence are cutting back as well.

You have more time than money (probably) so use that time to do this work and fix up the room to look very nice.

. - You may be surprised to know that many countries outside US speak extremely fluent English and can handle customer service better than most.