We had the same situation...a home in FL and one in MA. We are both from MA and bought a second home in Fort Lauderdale in 1995...in 2008 I moved my business down there for tax purposes and became a FT Florida resident, although my wife traveled with me every time I came to Florida she elected to remain a resident of MA. We had two cars, the one we kept in FL we registered in FL and I registered to vote in FL. Wife wanted to keep her MA residency for Health Insurance reasons, keep the doctors she had and she was flying up frequently during the winter for elder care support. We were still 'snowbirds'...both of us could work remotely, but also had to travel for business. Back in the 90's you could keep your out of state driver's license and get a "Florida Only" license (no more). You can only have one Homestead that gives you a tax break. There is no tax deduction for homesteading in MA, so I was able to Homestead in FL in 2008. I believe the rule at the time was that if you had a Homestead in another state that reduced your real estate tax you could not homestead in FL unless you cancelled the other. For a few years the State of MA contested why I wasn't filing a joint state tax return with my wife and they wanted verification that I was actually a Floridian...it had nothing to do with how many days I lived in either state....a copy of my FL voting records, valid drivers license, phone bill and water bill was all they needed. We had the option of filing our Federal taxes jointly or married filing separately (which one year was a huge advantage). Car insurance is something that you need to shop around for. I found State Farm to be as expensive as MA was...I now use Triple A and they cut it in half. My wife became a Floridian in 2012, and we simplified our lives by selling our MA property in 2015.
My tax attorney told me not to worry about having an out of state license or out of state plates...the borders between all the states are open
Hopes this helps
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