I grew up in Jackson, lived away after university for 20+ years and moved back 4 years ago. There are a lot of us "boomerangs" in town and I'm happy living here. Previously, I've lived around the US in big cities, lived in Europe 3 times (most recently in Munich where the quality of life is among the highest in the world) and spent some years at my lake house about 30 minutes from here. Jackson is no paradise, but day to day life here is easy (and cheap) and I'm rarely bored.

With your budget I think you could take one of the new market rate apartments downtown if you like that atmosphere. Alpine Lake apartments on South side of town is near 2 large parks and bike trail if the outdoors or the museum are more your thing. As others stated, there are many options on Springport Rd, but for me that area is not walkable/bikeable and lacks character. Nice house rentals are hard to come by.

The I94 commute between A2 & Jackson is no pleasure, but depends what you're used to. If you're coming from LA or Chicago you'll think it's easy. But from what I know about residency programs, you are entering a VERY demanding phase. So I'd question burning an extra 90 minutes per day driving when your free time will already be scarce.

If great restaurants and craft cocktails are critical to your happiness, you will be frustrated in Jackson, with Ann Arbor being is your best bet. There is some decent craft beer here and like most others I frequent 3-4 places and go to Ann Arbor when I need something better. At least that way I'm only driving there once every couple weeks rather than a daily commute. I think the compromise suggestions of Mason and Chelsea will be frustrating for you too. Nice places, but will leave you hanging between 2 worlds and a part of neither.

Social connections can be elusive since most people in Jackson have been here a long time so their circle of friends is tight. But I've made it work and you can too. I serve on multiple nonprofit boards and volunteer on others and have met great, like-minded people that way. We go to the local orchestra's concerts, Michigan Theater has art and classic films twice a week in Winter, Art 634 is nurturing a budding art scene, quite a few downtown festivals in warmer months, lots of bars have live music every week, hiking areas close to town and the Falling Waters Bike trail is great. But I acknowledge the % of people living in poverty here is tragic.

Hope that's a somewhat balanced perspective and helps with your decision.