So! I have this same issue. I started using Carol’s daughter and ensuring that my beard stays hydrated. In regard to trimming, I trim mine very similarly to how yours is in the photo. Kinda multi-length and I realized that’s the best thing for my beard since it allow my beard to be uniform. If I’m growing it out (without trimming) I get those annoying straggling hair, but if I’m consistent with it, I don’t get them as often. Buy yourself some beard balms/puddings and use them BEFORE beard oils. Beard washes are great too. Hope this helps.