Here is my rule of thumb. Flatland riding like I have around Davis means a road cassette with very closely spaced cogs. 26 is the largest cog on my flatland bike and typical 50/40/30 chainrings. I have a lot of minute choices to fine tune my cadence on the flats but no cliff climbing gears.
For hilly and mountainous rides, I opt for a bike with a touring style crank and an mtn cassette. The chainrings are 48/36/26 and the cassette is a typical 34T 9spd which gives you a high top end and a low bottom end, but not minute increments in the middle. The only time I notice "missing gears" is when I use this bike on the flats because of the wider spaced cogs.
If you are a good wrench and have a derailleur and chain that will handle a larger cassette, there is no reason you can't swap cassettes when necessary. I swap out the 34T cassette for a 12-25T when I really want to use that bike on the flats, thereby giving me the narrow range.
I believe in using gears to get you where you need to go, not attempting to strengthen your legs to match the gears. The latter can be very discouraging and perhaps damaging. There are so many anatomical and physiological reasons for each of us to be able to turn over a particular gear that I hate to see people told to "just get stronger." Low gears get you up a hill while you get stronger and then can use the next gear up. Plus, it never hurts to have a "bail out" gear.
Frends know gud humors when dey is hear it. ~ Da Crockydiles of ZZE.