O'Malley's also bringint RENEW International into the diocese for the next three years -- I understand that though they've been reined in to orthodoxy, they are truly hostile to latinizing in any form.
“I’ll try — but O’Malley is truly opposed to it, and I’m sure he can (and will) make things difficult for any priest who wants to do the TLM.”
If the Bishop tries to obstruct a Parish that wants the TLM in their Church, the local priest and/or parishioners can appeal it higher up to the Vatican. The instructions for this is in the motu proprio. In other words, you can go around any Bishop who attempts to thwart the will of the people and priest of any Parish that wants the TLM. When you feel more cheery, read up on this, and check with your local priest.