@Hammerojustice I decide to bring the answer to your question over to this thread. I actually had the morning glories (just a plant on each corner of two cattle panel trellis with luffa and lemon cucumber on one and squash and 1500 year old cave beans on the other. They were all just as happy as could be.
It was my first time growing beans and only did about 6 plants and boy is that variety prolific.
The best pollinator is going to be in my opinion is going to be borage. Mine got big and leggy and grow similar to tomatoes so you may want to put them in tomato cages. The bees love them. Since they will self seed, I had volunteers all over the garden year 2) you can ws them when ever you are ready.
I am putting my containers in one of my raised beds this year to get more sun. Last year they were in a more sheltered area (worried plant mama) and I think they will do better with a little more sun.
My best advise to a first time winter sower is....it is a simple process that we all try to make a lot more complicated than it needs to be the first year. The biggest lesson learned first year is be patient and don't toss what looks like unproductive pots. They do not all germinate at the same rate.