My daughter started taking a 30s bus across town from Capitol Hill to Hardy Middle School in Georgetown in 6th grade when it became clear she could meet up with other kids who were going about the same time. We would drive to the Eastern Market stop and wait for other kids to show and then put her on the bus with them. If they didn't show, we might drive her to school. It worked okay.
I have to say that we were nervous about it but I also felt that nervousness was a luxury of being middle class. We met kids going to dd's school who took the bus from east of the river at quite an early age because their parents had to be at work and couldn't drive them across town. I often wondered if I was worrying too much about dd at the time. I don't know the answer to that. (Now of course the child, who is a teenager, runs all over town on the red line and orange line. Can't keep her home.)
Is the 5th grade sibling already comfortable on the metro and bus? What neighborhoods will they go through? Could you do a dry run? If the sibling is comfortable traveling via mass transit, I'd look into it.
Also, does the sib have cell phone? Get him/her a verizon which works on metro or get him/her unlimited texting capability which you can also do for free on the metro (but I'm not sure if it's true for all phones but our sprint phone does it). When our dd is coming home late at night, she texts us from a couple of stops away so we can walk over and meet her at the station. Texting is a great way to keep tabs on the kid.
Hard decision to make, I know. Good luck with it!
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