Thank you so much for posting this question, I know filing in two different states can be annoying.
1. If you work remotely from CT then you should be only withholding for CT.
2. It will not complicate you taxes anymore than usual so it is ok to do that now.
3. It is completely ok to drive into MA for a meeting there is no need to change your withholding for a few meetings per year.
4. MA PFMLA is only available to you if your company continues to pay into it. MA PFMLA is different than withholding state taxes.
