I have a gauge on my "workshop" pump. The gauge is at floor level and I cannot read it very well from a "pumping position" but it has an adjustable red needle marker and I can see when the pressure indicator needle reaches it. My tyres are 32mm Vittoria Randonneur marked with a maximum inflation of 70 psi (iirc). I have set the marker on the gauge to that and I pump up to that (approximately). I give a "thumb check" before I go out on the bike and when I think it feels too soft, I pump them up again (so not often); more often than not, this is precipitated by me thinking that rolling resistance has fundamentally increased (my current tyres are the very slow version of the Randonneur). The pump gauge often shows them as below 50 psi when I go to pump them up (so you can see that I'm not fussy or particular about running pressures). My Lezyne Micro Floor Drive travel pump also has an (inline) pressure gauge (on the hose and even harder to read but I can see when the pressure indicator reaches a marker made of yellow insulation tape). It's readings always concur with the workshop pump. Presta valves.
I have to say that my giving the tyre a squeeze is not a very good indicator of the pressure. I reckon that anywhere between 55psi and 75psi, I would be pushed to know the difference, especially if not having something to directly compare it to at the same time (e.g. having just pumped up one tyre to 75 psi and then trying to gauge the pressure of the other tyre by feel alone).
