New York) and heading to tax-friendly states like Florida.

New York is very different.You can get owner occupied homeowners insurance on 1 to 4 unit homes. 

Investment Info:Large multi-family (5+ units) commercial investment investment in New York.

You don't specifically detail your real estate experience and I am a strong advocate of self-management when at all possible (rental experience, good legal guidance, a good understanding of tenant psychology - at a minimum) but you couldn't pay me to have a rental in New York. 

If I follow the trends I shall invest in Oahu but for my very personal reason, the Honolulu/Waikiki area is the latest area I want to visit, don't like it there, it's like New York City in Pacific.

You should talk to some local New York lenders about bank statement loans.

I’ve found a great property in the Western Upstate new york area.

Many visitors to Tulum live in a crammed small apartment in the likes of New York or Toronto and the last thing they want is to spend their holidays in a very small place.

You will definitely make more than long-term rentals.Things to consider:It is illegal in New York state I believe, and you'll want to look into legislation and possible legislation in your state before you make an investment.As someone pointed out, neighbors will notice.

Investment Info:Small multi-family (2-4 units) buy & hold investment in New York.