I owned rental real estate for years (1997-2016), but never vacation properties, strictly houses that we rented to tenants.
Having tried it both ways, I HIGHLY recommend using a good property management company. They will do things for you like vet the tenants, answer the phone at midnight when the toilet is backed up, and have a roster of people on hand to handle repairs. They should also handle all routine maintenance for you, so that the property is kept in the proper condition, instead of lapsing into poor repair. Finally, they should know local laws and regulations, so that you do not inadvertently violate the same. Ending up on the wrong side of a real estate dispute with a tenant is a pain in the ass at best. If you are not going to be in the same town, I would say a good property manager is critical.
Make sure you can afford it when it is empty. My experience has been that by using a good property manager I have found good tenants who stayed for years. You cannot count on this. If you don’t have someone in there paying the bills, make sure you’ve got a fund in place that will cover the bills.
Make sure you can afford to maintain it. The property will need periodic repairs (sink, A/C, gutters, stove, etc) and periodic maintenance (paint, carpet, landscape). If you don’t do this, it will decrease in value, and you will also be able to get less and less rent (or no rent at all). Make sure you are prepared for a hit in the rent you see periodically (on occasion without budgeting for it). You also need to budget for needed maintenance on a regular basis.
Talk to a tax person and get their thoughts on how to best set up your situation. Your rental will have implications for you.
Talk to your insurance person and get their thoughts on the best way to insure yourself. We carried a rental policy on the rental property and a large umbrella policy to cover personal liability. It wasn’t expensive, but it seemed wise.
My final two cents: vacation rentals are tempting because you can often get more on a short term basis than you can with a regular rental. You will have additional costs (such as furnishing the unit and finding tenants). If you want to go the vacation rental route, look for an area where that unit could be easily shifted to a non-vacation unit should the need arise. An example might be a college town, where students could be a long term rental demographic should the economy tank.
My personal preference is to have a stable, long-term renter in place, rather than fuss with vacation renters. Income is steadier and chance of damages is lower.