As a rule of thumb, I believe that if my velocities are over book, then so are my pressures. I have no way to prove this without pressure gages, but as a general rule, there is no such thing as a free lunch. If it is faster, than it is higher pressure.
This is a very difficult question. Physical signs are crude and inexact predictors of pressure. I do believe that sticking cases, blown or leaking primers, and loose primer pockets are 100% proof of an over pressure condition. But I also believe that you can be running "over pressure" loads and not experience these signs.
The cheap chronograph is a new tool that has only been around for the last twenty years or so, but for most pressure readings we are still back in medieval times, expecting that pressure is evidenced by physical conditions. Primer reading is no more reliable than reading tea leaves, but, in the transition from round to flat, you know something is going on.
I lubricate my test cases seeking to fully load the mechanism. When I see the transition from rounded to flat primers, I am confident that I am near, at, or over pressure. Dry cases in dry chambers provide anomalous primer readings. Also, parasitic friction between a dry case and a dry chamber hides over pressure conditions by reducing the load on the bolt. This happens all the time, guys develop loads with dry cases and dry chambers and they get a little oil on the chamber or case and then they start having stiff bolt lift. Well their loads were always overpressure to begin with, case-chamber friction reduced the load on the bolt, and fooled them into thinking their loads were under maximum. However, in recent testing in a 270 Win, I was getting velocities over 3100 fps with a 130 and bolt lift with lubricated cases were fine. The primers looked fine, everything seemed fine. Later I found some of the cases had slightly expanded pockets. Expanded primer pockets are 100% proof of excessive loads. I decided that velocities over 3000 fps were overpressure because pressures in load manuals are maximum just around that velocity.
For target shooting, I develop loads at the range, take my best guess as to whether they are over pressure or not, and then shoot them in matches. If I get sticking cases, leaking primers, then I know the load is too hot. Loads developed on the bench have shown over pressure conditions on warmer days, or days I have shot rapid fire, where the rifle gets a little warmer. If I get overpressure conditions, I cut the load. For a case about the capacity of a 308, I cut by half to a grain, until pressure indications stop.