I didn't say $200 and OP specified MIT, not Kendall. I know that 55 Franklin St is $375/mo. OP said that they're paying $67/mo in tickets, but that seems shockingly low considering they're illegally parking every day and Cambridge tends to keep track of re-fed meters. Plus, OP said that they're often using the parking app which has an additional $0.50 fee per transaction so I was low-balling the $200 since they might be paying an additional $1-2/day bringing it to $220-240 + 67 in tickets = $287-307.

Yes, a garage isn't as cheap, but when you add it all together, it's not like it's crazy out of the price range. It's not like street parking is $20 and the garage is $375. If you were paying $300/mo and needing to set alarms to re-up meters and such, $375 to have stable, legal parking doesn't seem crazy.

Heck, for a lot of jobs, you're going to have to pay for more than 8 hours of parking between walking to the office and getting back to your car at the end of the day and your lunch break. It might be 9-9.5 hours. At 9 hours, we're talking $225-275/mo plus tickets = $292-342.

Something doesn't quite add up with OP's math for me simply because it seems like they're still paying a ton for parking while putting themselves in a really stressful situation. Plus, the idea that OP is only getting 2.67 tickets per month while illegally parking every day seems crazy. OP has said they see parking enforcement circling areas so they aren't parking in an area where they'd be noting that their car hasn't moved and should be ticketed even if the meter has time on it.

It seems like the 55 Franklin St Garage would cost 0%-40% more, depending on how accurately OP kept track of parking tickets (the $800 number just seems really low). Even assuming that $800 number is accurate, we're still talking $267/mo if they're always feeding the meter perfectly on-time and wasting a lot of time waiting for that perfect timing all the time. Imagine someone scheduling a meeting and you're like, "sorry, I have to leave the meeting, my meter expires in 5 minutes. I'll be gone for 5-10 minutes." So, they're probably using the parking app for $1.50-$2/day in additional fees. That's $297-307 right there. If they need more than 8 hours, they're going to be paying at least an additional $10/mo for another 24 minutes to cover a very short lunch break.

I'm not saying it's as cheap, but when you add up all the costs, it starts getting pretty close. It's probably easier to ignore the 50-cent app fee and the $1.25/hour, but it adds up. I guess part of it was just curiosity about whether OP was working an irregular schedule or something because the math didn't seem to work out well in their favor. In the rosiest regular-work situation, the garage is 40% more expensive (8am-4pm with a 0-second commute to work, no lunch break, and never paying app fees). Maybe I should have written out the more realistic case where they feed the meter sometimes, use the app other times, have a lunch break, and have to actually get to their work/car. It seems like OP has to be spending at least $300/mo or 80% of what a garage space would cost.

I'm also just curious what they're doing. Are they parking, feeding the meter, then using the app to get another 2 hours in the same parking space, moving the car at lunch and feeding a new meter, then using the app to get another 2 hours in the same space (we're at 8 hours so far, but assuming a 5-10 minute walk from car to office and a 45 minute lunch break we've only covered 7h5m-7h10m of work and haven't left time to get back to the car at the end of the day). Are they then leaving work early or moving the car again and feeding a new meter? And when you're doing those switch-overs, you're going to have to either have overlap or risk a ticket - people can't time getting to a location precisely. One has to assume you'd need to burn at least 12 minutes covering the overlap during a whole day (another quarter). It just seems like such a production that it feels like there's information missing - like that OP only commutes into work 1 or 2 days a week or that OP only works a couple hours a day. Otherwise, a realistic accounting of the costs just doesn't seem to be that much cheaper. The ticket issue is more an annoyance compared to the rest of the production and costs. I mean, 9 hours of parking (8 hour work day plus time to get to/from car, time to cover car movement during the day, and lunch) + 12 minutes of wasted meter time + 2 50-cent app fees + $67 in tickets is $317. Part of me wonders if OP is even noticing the money they're spending because it's coming out $1.25-1.75 at a time. They've noticed the tickets, but they seem to have missed the huge amount they're paying the meters.

It's why it seems like there's more information to complete the picture on why a garage is so much more expensive. Yes, it might be more expensive, but it seems like OP is going for something that's at least 80% as expensive (and probably even more) while having a ridiculous amount of stress about it.