Anne Bancroft day on TCM

I'm back to my usual amount of time on Twitter. Mel Brooks (really) tweeted that today is Anne Bancroft day. He said he was particularly happy that they are showing "To Be or Not to Be" because they played a couple in it together. I have set up to record it, as I hope to be asleep when it airs.

Must I get more estimates?

I finally have an estimate from one highly recommended painter, to do the outside of the house. It is many dollars. I knew it would be many dollars, I just didn't expect quite that many (almost $19,000). It has been an unreasonably long time since the last time it was painted, so I am kind of spreading it over years, but zowie. As a responsible person, am I obliged to get other quotes so I can compare?
If I do get another estimate and it's wildly different, do I just choose by price? If the estimates are close, how do I choose which company to go with? I'm a grown-up who has been arranging for house repairs for decades. Why is this hard?

Too secure?

I am already registered for a half marathon in Maine in October (as previously mentioned). Some NY bellringers are considering the Philadelphia half marathon a month later. Would it be ridiculous to do both?
I was just looking at the race website and was a little shocked to see that one has to allow extra time before getting to the 7 AM start because everyone will have to go through an x-ray machine and/or be wanded. If you bring your own water bottle it has to be empty, which means I guess non-human stuff will be x-rayed also. I don't know exactly why I am offended by this. I do other things that require zapping - I had to do all that last week when I went to stand outside the governor's office.