Of course you can sue! The questions are really, a) can you win? and b) which jurisdiction should you select.
a) depends on the strength of the Notes and record keeping;
b) depends on where the debtor's assets are located. You can sue either where you live, where he lives or where the transaction occurred. However, since your primary interest is in collection of the money, not the suit itself, I'd follow the money trail for your choice of venue. You can domesticate foreign judgments, but why bother with the extra step and time if it can be avoided?
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You should hire an attorney in Florida to try and collect this debt. Choosing Florida will get you closer to his assets and income sources (bank accounts and wages). Good luck.
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The answer depends on the incurrance of the debt. Was it incurred in NY? Was it for purchases he made in NY. Did he sign the Note in NY? What I am getting at is whether we could establish jurisdiction over your ex-friend in NY. There are many indicia considered by a Court. I would need to discuss this further to give you a more solid answer.
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