Do you ever take a transportation because a "deal" is offered? I feel like a sucker but I do whenever I see one
Yes, but the problem is modern day travel pricing is demand based, and prices go up and down constantly making what is a "deal" very unclear (YMMV)
I started buying random train tickets and going on day trips to random places when my local train company was nationalised, because I was such a huge supporter of this being done. I never went anywhere when the trains were privately owned.
In both cities I've lived, bus service on New Year's Eve and Day are free, so I usually get over my fretting about whether to go or not by telling myself at least it's free to move around.