Why? He can just as easily file in MA through the internet. While MA may be slow, FL's adminstration of a claim leaves a lot to be desired.
Why? There is no legal requirement to do so. I tell people to file the claim in the state with the more forgiving UI system as in forum shop. I've had people get some very pleasant surprises.
Even based on what you're telling him to do, it makes even more sense to file in MA. If he's successful at getting a temp job in FL with a qualifying separation to purge any disqualification, he'll be able to draw his 30 weeks of MA benefits, and THEN when that runs out, he'll be able to use his MA lag earnings plus the FL earnings to get a 2nd back-to-back claim even though the FL claim will pale in comparison.

