Be sure to team up with an agent that knows the area and also the investment strategies that are best for that area.

There are a couple of things that I would think about here, the timeframe you want to work with this agent (can be 1 month or 2 months or a longer time), whether you could do it for a specific area/city/town, or you could do it for a couple of properties you see.

Here's some input to help guide the decision between selling or renting the property, considering the specifics of the property and the potential additions like the ADU (Accessory Dwelling Unit):1.

A solid property management team (or maybe multiple PMs if your portfolio is large enough) is a must for out of state investing.

We have a team there that makes us quite efficient.

Very neighborhood specific. 

Quote from @Tanner King: Where are the best places or best ways to collect data on specific markets?

Also, nightly stays should be adjusted based on your specific pricing strategy as well (e.g. longer stays further out, shorter as dates get closer or gaps exist).

Sounds like you are already on the path to being an out of state investor and with the right team that can be powerful.  

RE Brokers in the area are a key team member as they should know the area, good rental areas, and they will be a good resource for rentals (possibly, if they deal in rentals).