Obviously, that does not apply to every single market on the Caribbean, but generally speaking, it does.Cheers!

@Shivani Brijmohan, while I cannot speak to NY, I will say in general:You should know how the property will be reassessed when you buy the property.  

I would regularly update your photos to reflect seasonal changes or recent upgrades, ensuring they are high-quality and well-lit.

And if any speak ill of it there billed a Nazi Fascist Bigot...... 

Throw in some extra costs like moving expenses, professional photos (a cost the STR PM may also need to pay depending on the quality of the existing photos), renter's and lessor's insurance and a listing on furnishedfinder to round out some of the start-up costs.

I suggest you look for clarity on what resources you can use or companies can assist in using a small piece of that equity as a downpayment on another high-quality asset like the one you already own.

You are required to file a complete and accurate return, which means reporting the income that you earned along with atleast the direct expenses that you incurred on your rental.There are two comflicting forces - Your tax accountant wants to be aggressive with deductions because it will entitle you to paying less taxes(now or in the future).Your lender wants to see as much income as that will increase your Debt to Income Ratio(DTI).The good thing is that you can speak with your lender about 'one time expenses', that were only incurred in that year and are not reoccuring. 

Ask agent to do final walk-thru video to send to you to confirm quality of work BEFORE final payment to contactor.8) List the property for sale.NOTE: we're heading into winter/holidays when all real estate activity slows.

Quality contractors already have their plate full . 

@Scott ChampionRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?