Personally, I don't really look this much into it. I collect these figures because I enjoy the films and the characters, and these figures have some of the best likenesses and details that I've ever seen on a collectible. If there's a figure I like and I feel it's worth a particular price to me, even retail, I get it. If the price curtails later on, I don't beat myself up over it because at the time I got it, it was worth X amount of money to me, so enjoy it. If I'm not willing to even spend retail price on a figure that I can live without, I don't get it. If I see it later on at a low price, sure, perhaps I'll get it because it'd be cool to have. But it's not worth above X amount of money to me.
It's really that simple. Simply how much something is worth to me. The only person making the decision to buy these is myself. It's not like I'm being coerced.
I'm jumping on the opportunity with Han and Chewie because HT is releasing them again. Could I have gotten them on the after market because I missed them the first time at retail? Sure, but it wasn't worth $350+ to me, hence why I didn't get one. I probably never would have if they always remained that price and I would have had to just settle with that. However, they're being released again at retail, so I'm taking advantage of it. I personally don't think I'd pay over roughly $275 for a Solo. That's how much he's worth to me.
I mean to me it's not that hard; you like a figure, you get it if the price is worth it to you. If you don't like it, or you don't feel the price is worth it to you, you don't get it. Simple as that.