As someone who didn't live here at the time, can you please explain how
exactly Mitt Romney got elected as MA Governor? Looking at him now, he
just doesn't seem to have the ability to connect with people.
It's a fair question -- and as I have previously reported, the campaign became aware pretty early on that you can't make the electorate like Romney, so, as you imply, he had to somehow win without that connection with voters.
But the Massachusetts electorate is not as liberal as people think, and they like to elect tall, good-looking Republican men to major statewide office (Charlie Baker excepted -- to date). Romney was able to exploit some issues and stereotypes to make people think that Democrat Shannon O'Brien was soft on crime, weak on oversight, and mostly in favor of abortions for children.
This is more or less the approach he's taken in campaigns ever since; the particular issues and stereotypes he exploits varies according to the specific opponent, but that's always the basic strategy.