I have recently been thinking about starting up my first fig over here in MA, and I'm trying to find the right match for my desires. I have south-facing windows which let in a lot of light, and so the thought was to keep a container fig which I'd bring in during the winter. So the question comes to what would be the best fig for me. I have been considering Celeste based on how hardy they're supposed to be, but I'm seeking more input. Are there any fruiting figs which take to being inside more than most? Where can I obtain cuttings?

Welcome to the forum.  I live in the south so I really have no advice for you but there are many very knowledgeable people here.  I'm sure you will be able to find everything you need to know.

Probably the best idea is to let the plant go dormant for the winter.
That is what most northern growers do.
put in an attached garage, or cold room, less than 40 degrees,
or plant outside in ground and winter protect.
Keeping plant in doors and growing will probably require additional lighting to keep it healthy and not spindly.

As Grant said it would be best to let your tree go dormant. Since you have a sunny south window you could bring it in about February to break dormancy to get a head start on the growing season. That would help for the late ripening types like Black Madeira.

And if you let them go dormant you can have as many figs as your garage can hold.  At least 150.  :)  Hardy Chicago, Nordland and Florea are much more cold tolerant than Celeste.  At the top there's a thread called 'start here'.  In that there's a link to 'best figs in your area'.  That makes good reading.  Some figs taste better than others, some produce fruit earlier than others.  It's good to have a few to extend your season and have a variety of flavors.  If you end up liking more fig plants than you have room for you can always graft varieties on to one another to make a 'fig salad' tree.