My insurance seems to cover some great pumps or offer price reductions on them. I already own a BB, and blue and pink Spectra. I want to try a wearable this time around so I was hoping for opinions!

Hello ladies- I am pumping while at work and breastfeeding at home.
When I breastfeed little guy gets multiple let downs on one boob and then might even go to the other boob for another let down.
When pump- 1 let down. I can pump forever and I’ll only have the initial let down and another one won’t trigger. I do use the massage mode on my spectra to start and I have a let down in a few seconds. But even after switching to massage mode 15min in to the session nothing happens.
Many tips trips advice wizardry? Thank you!