I wouldn't put "clones" and "reliability" in the same paragraph I hear what you're saying regarding the NES, though, the ZIF mechanism can be pretty obstinate. Does anyone really struggle with Megadrive/SNES, though? If I have to try a cart more than once or twice, that's a bad day. Amazing what a bit of isopropyl alcohol can do for dirty contacts.
If you must get something. Get a Neo Geo Pocket Color (not a NGP as it's only b&w). Amazing handheld with some great games for it. But be warned you must love SNK or fighters as that's pretty much most of the library. But the sticks makes fighters soooo freaking great!
If you only have 30 Dollars, get anything 16 bit - or that Neo Geo Pocket Color, which is, indeed, a pretty awesome handheld. Or get a Dreamcast. That system is the coolest ever.
