Yeah, moving things around can be annoying. I often cut wires, move a block (wire ends included) and reconnect. Silly.
In general, consider spending a good bit of time on each layer of the PCB file. Copper layers are obvious and necessary, but the other layers are properly graphical layers, too. There can be issues relating to soldermask that are worth manual inspection. Silkscreen is all about how you want it to look; if you aren't putting in the effort, it isn't going to look nice, or be helpful!
I normally ignore silkscreen except for very early in the layout, and nearly at the end, as a finishing step.
I set all designators to a default size and position I like -- Center-Above, and 30/6 mil text for most SMTs, 60/10 for larger parts and THT, maybe 90/10 for large or important connectors, labels and notes. At the end, I shove labels around wherever they can fit, maybe moving some components to make room if it's not a problem.
Tim