I doubt you have a serious chance at retaining the governorship either way.
Why's that? Republicans have held the governorship for 16 years. Massachusetts voters still want an executive check on the sometimes out of control Legislature.
The serious wrinkle in Healey's plans right now is Mihos. If he runs as a Republican and pours a ton of his own cash into his campaign, that could spell trouble. Alternately, if he runs as an independent and does the same, he'll probably take more votes from Healey than from Reilly or Patrick.