@Jennifer Lee , my wife and I are doing the total opposite of you. We started with our vacation rental property and now looking into buy and hold properties.
We have a great 1bd/1bth condo in Kihei, Maui that is not exactly water front, but we are directly across the street from Kamaole II beach (about 50 yard walk or so). We bought this place because we loved the area and wanted a place in Maui. Although we went into it as an investment, it was more an emotional purchase for us. We really only wanted to get enough rental income to cover 1/2 the mortgage.
That being said, there's really no "down season" in Maui and we have far surpassed our goals and bring in between $28K - $30K gross a yr. With expenses we bring in on average 6-7% cash on cash.
We do have a property manager, which is onsite at the complex. They charge $5/nt for owner bookings and we do 99% of our bookings ourselves through our VRBO listing site. If they book any reservations, then they charge 18%. Being out of state, their services come in real handy if something needs to be repaired or a guest has any questions or concerns.
Pros, well it's been a better investment than we imagined, so far. Because of our location, we've been able to keep an occupancy rate of 89% for each yr (we've owned it since 2012).
Cons - Expenses are much more than on your run of the mill buy and hold property. Here's a recent thread where a member asked to list our expenses: Vacation Rental Expenses. Since we provide the unit furnished, there's also the extra cost to replace items due to wear and tear. We are replacing our sleeper sofa this year and it's only about 5 yrs old. We buy new sets of sheets, towels, beach chairs and other items every year. We had a new water heater put in this January. Because of the climate there, most of our fellow owners there change out the water heater every 4-5 years. Don't want a water heater to leak or blow while a guest is staying there. So lots replacement and preventative costs.
As you accountant mentioned, tax classification is important and the amount of days you personally use it is very important. You can use the property 14 days of the year or 10% of your occupancy days and have the property classified as an investment/ transient property. Lots of great tax breaks such as mortgage/ mortgage interest, expenses to maintain, travel expenses to maintain, insurance, PM fees, credit card fees, etc... If you let family or friends stay for free, that counts towards your 14 days. If you rent it out lower than market value (giving 50% discount to friends for example) also counts against your 14 days. If you break the 14 day/ 10% rule, then your property is classified as a second home and there goes all your tax breaks. I'm no accountant, so please make sure to go over these numbers with your accountant.
I hope this info is helpful. This is our only vacation rental we own and we've only had it since March 2012, so we are far from being experts on this subject. Let me know if you have any further questions and I'd be happy to answer them!