Hi all, thank you for your replies. I've been considering these suggestions and having a bit of a play with it - although I I've also found a spare moment to make a sample drawing to illustrate the challenges I'm encountering.
Challenge 1: Cartesian management of placed views
Can placed views be constrained or moved on the page in a cartesian manner? Surely they have page coordinates in the file somewhere, but I can't find a menu or means to control them numerically. Likewise, say I want to add an arbitrary dimension between the part on the left, and the part on the right. Obviously the actual number measured on the page is fairly interpretable/trivial, but in creating an assembly drawing, it may be important to annotate.

Challenge 2: Sketch snap points on drawings
Say I want to make a sketch that uses both of these parts as snap points. I believe any sketch created directly in a *.dwg can only interact with the part/view it's created under. Project Geometry seems permanently greyed out in any environment I can find, so any sketch created directly in a drawing ends up floating or "not quite right." I've made an example below. The diagonal line is in the sketch "No Parenting (top)" and cannot snap to any points on either part. The arc in the active sketch is parented to the lower part, snaps nicely to that but cannot interact with or snap to the top part.

Challenge 3: Annotating between parts
Okay, so here's a very rubbery example of what I'm trying to achieve. Everything bar the connection header parts at each end is manually added in the *.dwg. The diagonal lines have the aforementioned snapping issue, the alignment of the parts is questionable (I'm aware of the Place View > Modify > Vertical/Horizontal function, but not any offset or datum control), and perhaps most notable is the "especially problematic" dimension below. I've had to add the red line in a sketch to allow that dimension to be created. The red line is itself floating and not snapping to the intended points. I can hide the red line, but it definitely feels like a hack job.

The only workaround I can think of is making an assembly of the required parts and importing that as one to the drawing, so that the elements I'm trying to express in a sketch are replaced by 3D solids. I'm trying to avoid doing that, because I'd like a workflow for other employees which only involves updating a drawing, minimising the skill requirements and complexity of working with assemblies etc.