Anyone else hit this exact wall?

You have a 40MB PDF — technical spec, project doc, whatever — and you need to get it under 10MB for an upload. You Google a quick tool, drop the file in, wait... and then the download comes back with your architecture diagrams looking like this:

The left side is what most "free" online compressors give you. The right side is what you actually need.

The two things that always go wrong

1. Your vectors and text get rasterized