This looks very nice and useful!

While Trivago covers major hotel sites, I sometimes find “shady” small sites often times offer better prices for hotels. I’ve been using super.com and vio.com and they seems great.

Another complication is credit card companies’ own portal. E.g. we need to take into account Amex’s FHR or Capital One’s premier collection. They offer credits and sometimes special “stay two nights, one night free” stuff. If we are in the credit card game, then there’s also “I have X credits in the first half of the year so it’s free” situation (e.g. Hilton resort credit).

I like your inclusion of Obscura. I have a blog post of how I pick where to go to: https://blog.yanda.rocks/posts/how-i-plan-my-trips/ and my hope is one day I could automate that.