I try to make careful decisions. When I pay good money for a guitar, I want it to be a keeper.
The only time I miscalculated was with my Affinity strat. I bought it as a project, decided it wasn't worth it, and decided the 51 would become the project guitar. There are a few guitars I would like (Cyclone, Duo-Sonic, and eventually a Mustang) but I plan to be patient, pick my moments and hopefully own them all. And if I do have to get rid of a guitar, I dont want to regret it later on. No regrets about selling the strat.
Almost sold my Jagmaster - luckily my friend was lazy about putting it on ebay - and I'd be kicking myself now if it had happened.
edit: By the way, that is a seriously impressive bunch of guitars. What do you have at the moment?