Before GPS it was awful, and it wasn't until Streetview that it really got "fixed"
I arrived in Boston in 1996, as a dedicated user of the maps of the
Alexandria Drafting Company who made highly-readable metro area atlases for DC and Baltimore and others, but, unfortunately did not cover New England
So we had a mix of decent maps (AAA) and crappy atlases (Arrow, one spread per town, as if people didn't need to nav between villages!) where you'd have to look up a street and then use the A1 thru R20 grid, or whatever), and the early web directions from Map Quest and Yahoo Maps.
I was a dedicated paper map user until about 2010. Only with streetview could you really be sure that the 15 Beacon Street you were going to was the one you wanted.
But it sucked for reasons:
1) No grid, no Zero Milestone, no spine, no central crossing
...nor quadrants or East/West or North/South (such as "the other big cities" have NYC, PHL, WAS, CHI, BAL ) where you could learn a central street or crossing and work outward from it.
...nor water always on the same "side of town"
...too easy to lose your sense of direction at a series of 40 or 75 or 120 degree intersections while walking or driving
2) crazy-small polities
...which meant turning pages as you drove and greatly increased your chance that on the same paper map there'd be two unconnected streets with the same name, see 5, below)
3) Too many 1-way streets
...too hard to get "into" a neighborhood like Beacon Hill when 90% of the streets are one way flowing "out").
In the name of reducing cut-throughs, you'd usually have to loop around Beacon Hill twice before you found "your way in"
4) Too many small streets, such that you couldn't tell name or direction from a map (while driving)
5) Too many street names re-used without connecting to each other, specifically the ones that you'd find a lot of lost people looking for
- Cambridge St (Allston vs & Cambridge & Boston)
- Beacon (Boston vs Somerville vs Chelsea vs Waban)
- Summer St (Boston vs Somerville)
- Winter St (Boston vs Cambridge vs Arlington
- Willow (Boston vs Cambridge)
& any others where people expected that "Boston" wouldn't repeat the same street name from Boston Proper across the formerly-separate polities of East Boston, Charlestown, Allston, & Brighton
When I lived on Willow St (Beacon Hill) I'd regularly get people looking for Cambridge's willow. When I worked on Cambridge St, Cambridge, we'd regularly get people looking for Cambridge St Boston.
Almost every place else in America you can go, they've done less annexing and have more conspicuous boundaries