You will find everything you need to know if you are dedicated to reading these posts and listening to the podcasts. 

There are lots of FB pages dedicated to vacation rentals for sale.

Hey @Devin Bost, I would highly recommend a few things to help with this. 1) Have systems and processes lined out for any emergency you can think of.2) A spreadsheet of subcontractors/ vendors that could handle the situation that arises (plumbing leak, electric out somewhere, etc.)3) Your cleaning team and handy person should be utilized for some things.4) Something like Breezeway can give you 24/7 support around your property with a dedicated phone number line.

Decide how much time, effort, dedication you want to commit to your real estate endeavor.  

Dedicating certain evenings or weekends to handle real estate tasks like research, phone calls, or property visits will help you stay on track without becoming overwhelmed.

I agree that licensed agents will rat you out, as they should (my opinion)...licensed agents have dedicated lots of money, time, and training to hold the real estate license. 

When I was in Norfolk they had a housing assistance office where they would help Sailors find units for rent from their own dedicated list.

I've seen architects spec the wrong sprinkler system more than once and you either have to spend nearly double on a larger system with a dedicated water line or amend the plans (and potentially lose months depending on when the mistake is caught) waiting on the amendment to go through so you can move the project forward.

Awesome approach, it is best to meet with the agents in real life, see the neighborhoods and get the vibe in real life.I usually talk to them on the forum for about 6 months and then take the next step..to see how dedicated and professional they are .

Having a dedicated account for property-related income and expenses makes it easier to track and document everything for tax filings, deductions, and accounting.