We've recently updated our upload sessions to enable parallel upload of chunks. The team just updated the cli to incorporate this functionality after your report. Parallel uploads of chunks should substantially improve upload time and reduce error for these larger files.
The largest chunk-size possible with concurrent uploads is 148MB (the largest multiple of 4MB below 150MB) but we recommend 16MB or 32MB and more parallel workers to optimize the speed.
If you do use our latest patch to upload your content, we would love to know how long it now takes you to complete your upload! It is always helpful for us to know how these upload cases perform with our users.