Container tomatoes

Container tomatoes

I have two pots of tomatoes, one "big beef" and another "beefsteak." Both obviously large tomatoes.
I bought them as transplants when they were about 12" tall and there were 2 plants per pot. Currently they are about 2.5 feet -3 feet tall and in pots that are about 12" in diameter and 12" deep. I am going to move them to a 5 gallon bucket (with holes, of course) ASAP but I have a question. Since both pots have two plants, should I separate them into separate pots when I move them? They are about 2 inches apart and incredibly healthy. They have tons of flowers and I expect many baby tomatoes within the week.

Since they are going strong, should I keep them together in their pots? I know this will make for weaker plants, but I think they will still produce. At the same time, I am okay with separating them, but being so close together I am worried about damaging the root base, since they're obviously growing together.

Also, I know they're out of season, but I also have broccoli in the same predicament. I planted them from seed a few months ago (since I live in Florida, it wasn't too much of an issue) and they're thriving. I already split them into three pots and gave one away, but I currently have 2 pots with about 7 plants each, 1 foot tall. I have pulled many of them and I plan to continue separating, but do they need to be in their own pot?
Since I'm moving soon, they're not able to go in the ground.

Any advice would be much appreciated.
Wildflowers all over my neighborhood.

Wildflowers all over my neighborhood.

Tomato seedlings

Tomato seedlings

tomato bottoms turning black!  and bumps on the stem

tomato bottoms turning black! and bumps on the stem

My Room

My Room

Garden candy…

Garden candy…

New apartment!

New apartment!