I live in Long Island and everyday I hear of someone else say "I'm leaving this highly taxed place" for areas with lower property tax like the North & South Carolina, Georgia, Florida, etc. but there's still such a shortage of houses around here.

High Desert is our field our local experienced team is dedicated to making the buying and selling of High Desert Long Island real estate Agents an easy enjoyable and satisfying experience.

"As your island of knowledge grows, so do your shores of ignorance" -John Archibald Wheeler

Not sure what island you're looking at, but with $90 - $100k to put down on a home, you will be in great shape compared to lots of folks that end up purchasing.     

I am looking to either rent from or partner with Landlords here in Suffolk County, Long Island that own small 1-3bdr single family homes.

It's not a bad idea to have an STR as an investment as it if it does well for cashflow and it could also keep your costs low if you decide to home swap in the future when you travel but I haven't fully looked into this option yet.We did look at Hawaii since we go there at least every 2 years being on the west coast however, you'll need to consider if being on an island is for you. 

I am a licensed Realtor in Massachusetts and Rhode Island and I am also a buy and hold investor. 

If you can, then maybe you should, but also imagine there's an island real close they could swim to, which isn't ideal but they're not going to drown.

Kyle, I used my commission towards closing costs on my first deal in Rhode Island. 

I am new to this site and a newby real estate investor in Rhode Island.