I honestly think I'd look into digging a part of the basement under the building for a mechanical room if nothing else. Get the water heater, water meter, Furnace/AC, pump for the heat pump, air compressor and dust collector (if noise is an issue), and a few other odds and ends out of your way. It would also get the bulk of your water service below ground where surrounding soil can help prevent freezing in the event of power outages.
Since you're on main street, there is somewhere nearby, a water main, and it or building supply lines can rupture and flood basements. Typically rather quickly on main street, because there's usually a main there sized sufficient to provide fire protection for the business district, and even if the 1" service line ruptures it can bless you with an UNBELIEVABLE amount of water in short order. And, therefore you really don't want to store a whole lot below ground. Were I to do it, I wouldn't do it at the front of the building. The further you are from the middle of the street, the better off you are!
Mono-slant roofs are also problematic. I know several of the businesses up in Turtle Lake had issues forever because of snow loads, ice build up, and such. It's about impossible to keep those roofs together on old buildings up there, try as you may. They tried roll roofing, tried tar roof, tried steel. Couple of them finally leveled the outside walls up and put rafters over them. Simply got tired of fighting it over the years. The ones that did, said they wish they'd done it DECADES sooner!! In both cases they went in and insulated heavily over the old roof. No more leaks, and saw HUGE savings on heating and cooling
Biggest problem you're liable to encounter with that is watershed on adjacent buildings, which many small town main streets have an issue there. Even if you aren't dumping it on top of the neighboring building, dumping down their wall, or too close to the wall can cause issues in their basement. Both of the businesses in Turtle Lake had the room to do it. Might be something to think about before investing heavily in the existing roof, if you can get away with it David.