Definitely check the lease. Lots of leases do specify that you can't install AC on your own and there's nothing in Mass that guarantees access to cooling like we guarantee heat. Often landlords don't want people installing AC units because often people put large/heavy units and put all the weight on the window - or they're installing a support structure and making penetrations into the exterior of the building.

For the winter, the landlords probably have a good case argument that it isn't weather tight for a Boston winter and that they don't want the added weight of snow/ice on top of the AC unit putting more stress on the building/window.

You might be able to negotiate it with the management company. You have two units and maybe you can get them down to $45/each. It's just one trip for their service person.

I think they should reasonably come down from the $180 for 2 units, but I don't think it's a scam on gullible tenants, ACs should be taken out for the winter, and there are good reasons to disallow tenant installation of AC units - it's overprotective for sure in most cases, but there are good reasons.

I'm guessing the lease stipulates this and they're going to have to comply, but maybe it doesn't.

There's also the question of whether $90 or 180/year ($7.50 or $15/mo) is the hill one wants to die on. When renting apartments, one often doesn't get to choose the exact rent. If this is the one thing that's pissing you off about this management company, I'd ignore it. Would you rather find a different place that's $100/mo more? Maybe your place is over priced, maybe management is annoying about lots of things, etc. Or maybe it's not worth the fight. Plus, even if you rarely turn on the heat, it's still some money there and probably $50+ even if you rarely turn on the heat.

If it's the hill you want to die on, it's the hill you want to die on. However, if the rest of things are great, I wouldn't make that the hill to die on. Yea, it's annoying, but the cost is minuscule compared to Cambridge rent. What are we talking? 0.5% of annual rent at a time when annual rent increases are in the 5-15% range? I just wouldn't make it my hill to die on.