I'm thinking of buying a Condo in a fairly popular tourist destination a couple blocks off the beach in Hawaii.

There is a property down the street that was 700k and has 8 units but it was renting weekly to tourists for 8 months or so per year. 

Navarre is not as "over-discovered" by investors and tourist yet, but will be.

So that's good news because when growth is accelerating at the beginning of the year the chances of a recession in that year are practically zero, historically...so that's the good news, you are going to be in a good environment for the next 12 months and possibly longer because of a worldwide recovery that's happening, this is the real recovery that's happening now after 2008.

Rental income is not considered interest or dividend income so you may not have to pay any taxes to New Hampshire.However, as a resident of MA - you will be required to report worldwide income which would include your income from NH.Nowadays - proximity to your accountant isn't as important as choosing an accountant who is knowledgeable in real estate taxation.You should interview a couple CPA's on BP and see who you connect with.

You will likely only report the rental income/losses in the state the property is located in.You will then be required to file a PA resident tax return where you report worldwide income.

I made the tough decision of buying a less than desirable property in a up and coming area of one our tourist districts.  

You will report worldwide income on your resident tax return.You will also be required to file a non-resident tax return in the state that you have rental properties in.If you pay any tax in the non-resident state - you will receive a credit for taxes paid to other states on your resident tax return.

Being interested for Worldwide RE, both houses and apartments in apartment blocks.

It is full of tourists, the #2 destination in the U.S. for weddings.