I think the tail length is good because it's about the same as what it is when I use the regular trimmer on the machine that is at the end of the guided threaded path on the machine (no tail length adjustment in my machine system as well) but I think this issue has been with my machine since I got it about a month ago, just now understanding it more and noticing it. Using Simthread 25pcs 90WT White Prewound Bobbin Thread Size A Class 15 (SA156). No thread or debris in the bobbin area.
What I'm starting to notice is that the issue doesn't occur when I raise the presser foot so I think that the issue is the thread isn't being pulled down strongly enough at the beginning of a new object when it starts on it.
Again I want to thank everyone for the support so far!