That’s a broad subject in how you asked it, kind of not sure how to approach it…and Im the peanut gallery here so take my advice with a grain of salt but here I go anyways
If you are having some difficulty choosing which tricks to open and perform with in a street environment it is likely because you are still fleshing out a persona or character. Those really help inform you on some of your presentations and effects.
For instance a balloon swallow is a great opener for some street buskers, but not so much if you plan on doing a gambling act. I see you know the Chicago opener…a solid persona would help you choose a presentation for the trick, like is it a prediction? Magical change? Magician in trouble? No matter your presentation I think it’s a trick you should be using for now because it can be pretty interactive (I know some people dislike it, ymmv).
That being said, what helped me is sorting my tricks into ones that can be done for groups of 2, 4 or 6+(surrounded). Then I WROTE DOWN set lists for the situation and DID THEM. Doing this made sure I had a plan already when I was approached or vice versa. It also helped by me having a plan already to go if the group size changed. It also showed me lots of my material was terrible

My stuffs not great now…but it’s not terrible anymore

Writing your stuff down will also help you edit it later, both in your magic sets and patter.
Not sure if this is what you are looking for but if ya got anything out of this I hope it’s to
write down a set list for certain situations and do it.…work on your persona as you go.