Can't say I've ever really though about pressure, beyond the usual 'that primer looks a bit flat, might have gone too far here' type of thing on ladder tests.
I usually select powder purely on what's reliably available and single base out of the top 2 or 3 in the book for my round and bullet weight, and only change it up if I want / need more velocity, in which case I might move to something double base. Temp sensitivity is also a factor for some rifles.
Beyond that, I usually load to either achieve a target velocity, or to a load with a low ES, or to pressure signs and then back off a few percent to the maximum safe velocity depending on the intended application of the load. It's my experience that most loadings can be made to shoot pretty well by playing about with seating depth, crimp or neck tension after that and more velocity = better trajectory and more energy.
I'm also not sure tht there is really a reliable method to test pressure available to the average homeloader, so you can only go on what the book states for a given load, and on the rough visible pressure signs on the cases. Quickload is I suppose an indicator as well, but I don't trust it that much. I've seen the same load that works fine in one rifle (S&B cheapy FMJ as an example) give serious pressure indications in others, so it's my view that even slight variations in barrel or chamber dimensions can give fairly substantial swings in the 'real' pressures, despite the book saying that the load should be the same.
I suppose one could say that powders giving higher safe max velocities could give the lower maximum safe velocity of another powder with less pressure, but that generally just means I crank the velocity up a bit more...