There are several turnkey providers in town who can handle the process for you from top to bottom but you will give up some of the equity for the ease/reduced risk of the transaction.

Doing it this way allows you to ease your way in and costs you less up front - down payment for an owner-occupied property is much lower than an investment property, you may qualify for down payment assistance and can even use funds as a gift from a family member if that's an option. 

To recap: Be extremely cautious with flat fee MLS sites that only refer business to other agents.Bonus PointsYou should also consider the ease of use of the flat fee MLS listing provider, for example, can you complete everything online?

Ease off the gas pedal local governments, holy sh!

I also recommend one when unmarried partners want to invest together, for ease of tax filing if no other reason.Whether or not you NEED to put each property in a separate LLC is a great discussion to have with your attorney. 

Ease of tracking expenses for me and accountants is the other major factor for me on the software.I'm hoping some experienced voices could provide a sanity check, but if we can thread the needle financially this would be a win-win-win at a time when money is only getting more expensive.

Your best bet from what you said, for proximity and ease of use and volume of vacationers would like be in the Woodstock area or the Catskills.

Ease off the gas pedal will ya?

Overall the positives outweigh the negatives in my experience and what you lose in nightly rate you make up in occupancy/overall income and ease of management. 

As an out of state guy you want to buy something that will cash flow but also comes with ease of management.