I am thinkin' about a Hermes (Birkin or Kelly), but...

Welcome to the dark side. I can totally sympathize with your case. Not too long ago, I remember having heart palpalations after spending nearly $1K on my first high end bag (LV.) And boy, did I pamper that baby, lol. But eventually I grew out of it and used it like any ol handbag.

The same applies to my teeny H collection. I echo the sage advice of the other lovely TPFers about getting insurance.

Additionally I would suggest studying the reference thread and learning about all the lovely styles H has to offer. You never know - something other than a Birkin might sing to you. Plus aside from a Kelly, you can wear those styles quite regularly and not worry about attracting the wrong attention in your normal daily activities or holiday jaunts. And at these price points, you want to be sure of your purchase. Good luck!
 
I just agonized over my first Birkin purchase. The most I'd ever spent on a bag or clothing before was probably 2-2.5k, so this was a big deal. It actually kept me up at night until all the details were worked out and I was comfortable with it. When I get it, I plan to put it on the insurance and carry it a lot.

For travel, it will depend where I'm going. It will be much like I do with jewelry. If I'm going to New York, Paris, London, Istanbul, it will go with me. If I'm going to somewhere where I don't take my engagement ring or extra earrings (examples of past trips where these stayed home: running around Costa Rica or touring Vietnam, Laos, and Cambodia), then the Birkin will stay home and I'll probably take a Balenciaga.
 
I think after you start using it then the fear goes away
It was the same with me when i bought my first expensive bag, but when you start using it for real it actually becomes like a part of you.
 
I recently took a business trip and left my Kelly at home. I took my Evelyne and it was actually just perfect for my needs. I could drape it on myself messenger style and it was so comfortable and handy. I also used it for a trade show... took out most of my stuff and used the rest of the space for brochures, etc. that I picked up, etc. It was so perfect. My Kelly would not have been as handy as the Evelyne. I did miss my Kelly though and was glad to see her when I got home! Evelyne is back in her sleeper until the next time I need her!

I wouldn't take any H bag to the beach but rather would use a bag made for the beach in a canvas or other sturdy material and one that I didn't care about if it got ruined. I have a Longchamp Pliage that I use for my Kelly if going to certain restaurants, movies, etc. I do baby her and maybe once I get over the thrill of having her (will that ever happen) I'll loosen up a bit!