When Is It Worth It To Pay For The Added Convenience?

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My husband and I have always tried to be thrifty when we can, but there are a few times when we don't feel bad about spending the extra cash. Take yesterday, for example. A few times a year, we have annual events we like to attend in a city about 20 miles away from where we live. To get there costs about $45 CAD, in an Uber. Then there is another $45 to come back home. We are both legally blind, so we do not drive. We also get free bus fare here in our part of Ontario, because we are members of the CNIB (Canadian National Institute for the Blind). 90% of the time it doesn't cost us much to get around town. In order to get to the Serbian Food Festival yesterday, we could have taken a GO bus from home, which would have cost $16 or so, for a day pass, and then a taxi to and from the bus station ($21 each way). Unfortunately this comes with a number of inconveniences. First we have a 45 minute layover in another city, and unique to this week, our bus stop at home is out of commission, so we have to walk a quarter mile to the nearest stop. That problem should be fixed by August 1st. There's also a matter of timing. Take an Uber, we can go when we want. Take a bus, or a series of buses (city bus to station, GO bus to first stop, GO bus to our destination city) it's all about timing. This year for Serbfest, we decided to blow an extra 50 bucks, and just get an Uber! At first my husband wondered about this idea, but realizing how stress-free the day was going to be, he took to it pretty quickly. Also, we do not do it often. What's more, I'm here on MyLot, eh? I'm using this, and a number of other little on-line ventures to suppliment my income, to make these little things possible! With my bus stop still out of commission, I have an excuse not to go anywhere today (Sunday), and just stay home and "work" while listening to our favourite multi-cultural programs on the radio. Life is great! -- At which point do you decide that an expensive convenience is worth paying for? I should also mention that along with free bus fare, we do not own cars (obviously, because we're legally blind!!!) so there's gas, insurance, and general maintenence for which we do not pay.