I don't think it's worth doing the 100A line generally. Anything over 60A requires a shutoff switch, so you can do without that if you're running 50 or 60 lines. Also, the wire runs will be cheaper. Also, it's easier to install and work with thinner wire, which may figure into electricians' estimates. Since you are using wall connectors instead of an outlet, you could consider having one or both of them being sized for 60A, rather than 50. I'm thinking you said 50 just by default, thinking of a 14-50 outlet.
In general, I think having the higher amp charger in the car can be really helpful for bridging some gaps on trips sometimes depending on where you live, but having a high capacity wall connector with a huge breaker is usually overkill for at home. Unfortunately when I ordered my car, Tesla was only offering both bundled together as one package for about $3,600, which was pretty steep, so I skipped it.