This is another thing that fans of other things usually understand better than gamers.
"Legit": legal rights play a large part. If you make something original yourself it's legit. If you sell photocopies of it, they are legit. If I sell a photocopy of it, it's not legit unless you've given me permission. An old NES game is legit. Game & Watch Ball is legit. Nintendo's repro Game & Watch is legit. All regions are legit. An artist who is no longer legally attached to something he once worked on and goes it alone is...mostly legit. (Greg Lake and the ELP Experience). By this metric the Neo Geo X is legit, even though it's not that great, because quality has nothing to do with legitimacy. Vitage Ultraman SoFuBi are total crap but %100 legit.
Not legit: pretty much everything else. Home made shit. Neo Geo Freak, PCE Memories. CD-Rs of ROMs (yes, including CD-Rs of ROMs in a fancy case).
There isn't any in between. To most collectors in most scenes nothing bootleg is worth even the sum of its parts...dollar-wise, that is. In scenes where some kind of media or art is what's being collected then bootlegs are ESSENTIAL to that scene. There aren't enough copies of Sapphire or whatever to go around. However, all of these essential boots are basically worthless...
There are exceptions. Replica Group B rally cars are a big business now since almost any legit car described as such is half a million dollars now. It takes a lot of money to make one, and usually quite a few "legit" parts such as a shell and an engine, so these are by nature very expensive bootlegs. However there is ZERO confusion over what is real, and the real shit is hella super rare as f*ck. It would be VERY hard to build a knock-off 205 T16 and successfully sell it as one without having INTERPOL issue a warrant for your arrest soon after.
Neo Geo AES is kinda like the rally car scene in that the "boots" often require legit shit to make. For example, Crazy Dion is in the shit again for soliciting a fake Metal Slug JP. It has all legit ROM chips in it (making it infinitely more legit than anything Tobias does) but has all its PCBs and case and packaging either taken from elsewhere or outright fabricated. However, to the serious AES collector the cart is offensive because they SAC-ed a MS1 MVS cart and some home cart so make these so those two have essentially been destroyed (uncool) and used as a scam to suck $1500 out of someone (diabolical). The resulting boot is worth far less than the $100 worth of stuff they used to make it to a serious collector. Personally, as a collector of only the filthiest MVS carts on principle I'm cool with anything that has real SNK chips in it...but I don't do AES anyway...
In the record collecting world boots are just part of being involved in music, as a performer, as a store, a label, or fan. However, unless the boot itself is of some kind of significance (ie: secretly released by the artist, for example) then it's worth like $10 max forever.
In the record world there is no analog to Tobias becsuse in the record world the collectards aren't as collectarded as gamers are.
Which...should not surprise. Games don't exactly make you smart or worldly...