I'm a snob when it comes to revisiting an already smoked cigar. If it's sat more than 15 minutes I am grabbing a new stick. I don't get the time to sit with a stick everyday so when I do smoke I make sure I take advantage of it and make sure I enjoy it. If I am unsure of how long I will get to smoke but feel it may be cut short I will usually grab a shorter or cheap smoke so if it does need to die an early death than it doesn't make me feel guilty wasting one of my prized smokes. For me if I revisit a cigar that has sat a while it just tastes like an ashtray and is just an unpleasant experience. But like others said never put it back in the humidor. You are sure to taint your box and the sticks in it.
As far as being compelled to spend a lot of money on new sticks, Welcome to the Club. I know what I have invested money wise in smokes here at the house and it's kind of ridiculous but I assure you I am still ordering more although I could easily stop buying today and have enough to last me the next two or three years easy at the rate I smoke. For example, last Friday I ordered a bundle of JDN My Uzi Weighs a Ton and Wednesday scored a box of Cuba Libre Ones on C-Bid and contemplating ordering a 5 pack of 13s. It's a sickness and you my friend have it.
