Twenty-some years ago, when I was a single, grossly underpaid retail worker (though that job did provide health insurance, which would be far less likely now), I moved to Prospect Hill in Somerville. Until that point I had always lived "across the river," having spent my first few post-college years in Brighton, Allston, and Jamaica Plain.
Back in my Allston days I shopped at the Purity Supreme on Harvard Street (where there's now a TJ Maxx, I believe). Everyone called it Poverty Extreme and it was a brisk 15-minute walk from where I lived, but it was pretty much the only option in Allston. Food shopping in JP was even worse; there was a small, family-owned market called Flanagan's, but without access to a car, if you wanted to visit a Stop & Shop or Star you had to take at least one bus, or do your shopping on the way home from work. I did both, frequently, but carrying groceries on the bus isn't fun either.
After moving to Somerville I quickly learned that the closest, cheapest supermarket was the Demoulas Market Basket on Somerville Avenue just outside Union Square, about a five- or six-minute walk from my house. It was downhill to get there, uphill (lugging the groceries, naturally) to get back. Going there on my way home from work was again an option. (I know I could have gotten one of those granny carts, but I never got around to it.)
The laundromat was also at the bottom of the hill (both were a lot of fun in the winter), so another of my tactics was to bring my clothes down and get them started, walk over to Market Basket and get groceries, go back to the laundromat to switch my clothes from washer to dryer, carry my groceries up the hill and put them away, and go back down to retrieve my dried clothes. (I was younger then and had a lot more energy.)
I never grew to like shopping at Market Basket; I put up with it because I didn't have another option. It was always crowded, and the aisles were especially narrow. The store closed at 9 pm (and earlier on Sundays), so I had to plan ahead. The store felt antiquated and had a vaguely seedy air, and the deli counter people almost invariably messed up my orders. After I'd been dating the Mrs. a while she started driving me to a Stop & Shop, and after we moved in together we continued to shop there. (Now we live just down the street from that same store.)
A couple of years ago Market Basket opened a gigantic superstore in Chelsea, about a ten-minute drive from our house. It has a huge produce section, a substantial prepared-food area, on-premises baking, and spacious aisles that I never could have imagined while fighting my way through the throngs at the Somerville store. And the prices are still insanely low; we load up on hummus and pita chips there, because they're even cheaper than buying in bulk at Costco. I've also been buying bananas, seasonal berries, whole-wheat English muffins, local organic lettuce, and plenty of other items at wallet-easing prices.
They still close at 9 pm, even on Fridays and Saturdays, but otherwise it's a completely different experience than shopping in Somerville was. Well, it's still always crowded, but since the Chelsea store is so much bigger it's tolerable.