On the last fuel pump replacement on the Silverado, somehow I bent the fuel sender, so it's not been reliable since. I keep track using my trip odometer. When I get close to 280 miles I know it's time to fill up. And reset the odometer.
As far as starting problems...seems to always boil down to gas or battery. Went through this with some of my motorcycles and then just the other day my 356, which now has a new battery and some fresh gas.
The cure for all this? Drive 'em!