Due to an acquisition, my company needs to re-file my H1B - it is like an H1B transfer. My current H1B and my wife’s H4(and H4-EAD) all expire on 6/30/23. Should I ask my company to file I-539 for H4 concurrently with my H1B I-129 petition or should I wait till Jan 1, 2023(within 180 days of expiry) to file I-539 for H4 along with I-765 for H4-EAD based on my latest H1B i-797 at that time?
You can do extension of status for H4 with H1B, thay way it will be approved before the EAD expires next year. You can file EAD renewal next year before it expires and get automatic extension.