Hi Chris,
Personally I find it very frustrating and a time waster going outside without a plan. The sky teases me just when then the fun starts after viewing old favourites. I do though often go outside without a scope and learn/re-acquaint myself with the constellations- I find that's just as important as observing. When I first started out, for a long time, I used to (like yourself) stay in the one constellation and observe it well and still often do. It always ended up being a lot of fun and gives a more personal experience with that constellation. And because you spend so much time there, you get to know where things are naked eye, even though you can't see many of them without a scope, there's that great feeling of ah-hah I know what sits next to that star.
If you haven't already, and unfortunately Orion sets so early now, one of the best times I've had with exploring a constellation is Canis Major. It's packed with the most gorgeous golden stars, clusters, a blue/gold colourful double, and the biggest star we now of today- VY Canis Majoris.
My list is made around what object gets lowest in the sky first. It's preferable to catch them before they get to 30 degrees in the sky and get caught up in the atmospheric murk. I write down all my observations, and my list is sourced from a number of books, my main ones being Collins Stars & Planets (excellent resource of easy to get objects from a backyard) and Starry Nights software. I didn't go after galaxies for about two years, preferring to build up my observing skills with nebulae. It's a challenge after all observing from suburbia
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After doing lots of obs over the years of general things & running out of new things to observe under light pollution, I've moved onto double stars (still so many I haven't done), carbon stars (there's a ripper of one right next to beta Crucis known as Ruby Crucis, it's like a drop of blood! Use high magnification, beta is in the same field of view), supernovae when bright enough, nova and my favourite- comets and sketching them. Photographing Iridium flares, ISS passes, Moon/planetary conjunctions and of course the Moon. My new challenge is to take a pic of the ISS through the telescope, manually guided. So there's oodles of things to do up there, it never gets boring that's for sure.
I'm not sure how long/experienced you are with observing so forgive me if I mentioned some basic things
. Some years ago I did a couple of challenge lists in the observation forum. They're broken down into easy, medium and difficult. The May/June challenge is for the one constellation only- Hydra
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May/June
July/August