What tax pro should I see for retiring in Upstate NY?

In My Humble Opinion
1

So I have a Roth IRA, a 401K-rollover IRA, and a 401K, and live in Florida. Ideally, when I retire I would retire in Upstate New York. However, since it has a state income tax, I want to shelter as much of my money as possible from the NYS income tax, for instance by recharacterizing over my rollover IRA into a Roth IRA.

But I don’t even know who I should ask to see if that strategy, or others, would be more appropriate. Do I have to ask a tax pro who lives in NYS? Or should I be able to find a local advisor who is knowledgable about the subject as well?

2

I have no advice, but I’m just amused, as your retirement plan is exactly the opposite of many others (who retire to Florida after working in New York).

3

I don’t have any advice on taxes and retirement, but as someone who lives in upstate New York, uh…aren’t you doing this a little backwards? Everyone who’s in their 60’s here can’t wait to retire to Florida.

4

I grew up in Upstate New York and I miss the waterfalls/streams and valleys. I have a checklist of things I am looking for in an ideal community, and out of 20 or so points, any community in Florida will lose 5 points right off the bat for those as well as walkability, since you can’t very well walk anywhere in 95 degree heat no matter how close the stores are.

A funky hipster neighborhood in a downtown area could conceivably score higher than certain places in Upstate New York since it would score high in walkability and culture, but it would be too expensive. ETA but in Florida it would obviously score less walkability points than more northerly metropolises.

5

Again, not an answer to your specific questions, but have you thought of retiring to New Hampshire instead? Similar climate, but no income tax (although there is one on dividend and interest income, which is probably going to be a lot of your income).

6

I haven’t been to NH really and I’d need to physically go there in order to provide a good ranking.

But more on topic, does anyone know who I should go to to compare tax strategies and advantages for retiring in various states?

7

I took an eary retirement in Florida, then moved to upstate NY for several years. While I can’t offer specific answers to your questions, I can certainly empathize with your viewpoints on the relative attractiveness of upstate NY versus Florida.

Personally, I’d suggest rethinking your plans to avoid any possible interaction with the NYS Dept of Taxation. But if you do decide to move there, here’s a vote for Saratoga Springs as a “walkable” town with a good range of property values.