Yes, I apologize I didn't want to go on a long rant - so I tried to thin down the story.
I typed leg, but really meant return trip. (At least one of the cancelled flights did include layovers, the final attempt did not. I apologize for the confusion, I was typing this after calling US, getting angry after getting off the phone about the change fee, and having a few drinks.)

Outbound flight , attempt 3 - involved a stewardess and pilot fighting publicly in front of the passengers as well. While I felt awful for the stewardess, she cried the entire flight. She couldn't get through the announcements, and some folks thought that she was scared because of the equipment change out. Obviously, that's speculation. We actually hit a patch of strong turbulence that caused a long drop, and people were getting freaked out with the stewardess crying while trying to do announcements. (This is the first time I've ever seen the seat oxygen mask lecture while in the air.)
I don't understand why US would force an upset stewardess to fly. I realize that probably would have cause outbound flight #3 to be cancelled, but I was almost ready to give up at that point anyway.

I did get a flight voucher ($450) for the involuntary boarding of outbound flight #1, and this was regional small aircraft. I did tell passenger #2 that we could request cash, because I thought that was the case from what I've learned here. The desk staff looked frazzled when I mentioned it, so I let it go. I think there is a multiplier when you have to wait past a certain # of hours as well, so I'm not sure if the amount was even correct. $450 seems fair though, although at that point - I would have preferred to have been going home.

The 2nd outbound flight that US booked me on was a United one that was cancelled due to equipment change / and lack of crew (funnily enough at one point it said taxiing and awaiting crew simultaneously even though the craft had never left DCA), and this is the one-way flight that US is willing to let me rebook - if I pay a $150 change fee.

I'm pretty certain that weather was not inclement in either city at any departure time, but by the time I had left and driven many hours now overnight- it began accumulating on the highways in the mountains of WV. This was the only time I remember a weather situation forming locally- that's why I grabbed a rental car before I become trapped the next day as well, as the storm was predicted to move in the following day. And, as I said - I already had friends awaiting for me in DC.)

The desk staff at CRW were extremely apologetic and very friendly, the folks at DCA were not. The agent at CRW actually spent 15 minutes entering notes for me, so that when I called customer service they'd understand the mess that I endured.
One of the staff at CRW told me this happens every year- the regional aircraft can't handle all the holiday luggage- so they apparently endure this every Christmas.

I drove into a different airport (BWI) which is closer, and then took a cab home.
I was optimistically hoping I could grab Metro, but the mountain snow slowed down the driving and thus Metro was closed.

After I had requested the cancellation at DCA the next day, the DCA desk said that there was nothing they could do for me and I'd have to email customer service. Although the taxi cost the same (and under the marked limit), the taxi voucher was marked for IAD (as that's where the UA flight was headed) so the desk at DCA re-iterated that they could not help me. I probably should have escalated to a manager at that point, but I was so frustrated that I was about to lose my cool.

DCA was the original departure, CRW was the destination, so as you can see this was an expensive hour+ flight. Normally, I'd just drive during the holidays- but I wanted to spend more time with the family / friends not less.

So I figure I'm out the $60 one-way car rental, out the $70 taxi fare, now required to pay a $150 change fee on the return trip should I use that, out $50 in gas, and all the time wasted in airports.

The original DCA gate agent was confused, and thought I was going to Charleston, SC - not Charleston, WV. She had already began rebooking me, and like I said - I have some responsibility for that as well. This also delayed everything, and I was really annoyed when I realized the plane didn't board for another hour.

There were multiple flights per day, I'll follow up with the details when I start drafting an email to customer support. Is there a place where you can see historical flight status? I should have been documenting this all along.

This will be the first instance I've ever complained about a trip with any airline.