"Claim Jumper" writes in to ask:
Should supervillains have sidekicks?
Yes and no. It depends on what you're doing, and what your motives are. All of these things revolve around an important truth of villainy: You are in this for you, other villains are in it for them. Villains can have friendships, working partnerships, and so forth, but at the end of the day we didn't get into this gig for altruism.
Sidekicks are traditionally a hero thing, because heroes and sidekicks have compatible goals. Your goal as a villain is not guaranteed to be compatible with your sidekick's, so it's more likely to end badly if you try to emulate what heroes do.
I'm retiring but I want to apprentice someone
This is more of a mentor-student relationship than a "super and sidekick". In that case, what's in it for you is the feeling of accomplishment in training someone new to do what you did. Your trainee gets to learn new things, do his own capers, and profit from your experience. Provided you both have compatible personalities, this will work out just fine.
I want someone whose powers or approaches complement my own
In this case, you should approach another villain with about the same level of experience as you. Such partnerships don't last long unless both sides feel that they are equal. Bruised ego, damaged pride, and hurt feelings will end unequal relationships.
If your powers are such that you really need a partner, and all you can find is a junior, make absolutely sure you have a clear plan in mind for when (not if) he decides to branch out on his own. I cannot stress enough that such relationships are almost never stable.
I have a relationship with someone (romantic or familial) but have superior powers or experience
You can pursue this if the relationship has already proven to be rock-solid, and you should not plan for a long career as a villain team until you get some experience. You should mutually agree to one or two capers to test the waters, and only then see whether it will it should continue. Some romantic pairings try to invoke Bonnie & Clyde as role models to emulate. I want to point out that those two took totally unnecessary risks and eventually got themselves killed, because people together will do crazy shit that neither one alone would have dared to do.
I want a Mini-Me or Kid Hostage
No. This never works out for long. If you can't show respect to the person you intend to take on as a partner, they will respond to it badly, and you will lose out on whatever opportunity you had in mind. If you need a short-term decoy or something, don't waste the time building a sidekick, training them, or any nonsense like that. Use a random civilian instead.
Let's talk about a few example villain pairings and how they work out.
Needle and Thread - hired assassins who work the Eastern Seaboard. This is a stable business partnership. The two supers use different code names when working solo, and they come together to fight tougher opponents. They are mutually respectful and have complementary powers; neither one is a "sidekick".
Tellurian and Geode - this is an example of a sidekick-style relationship that went wrong. Tellurian was robbing banks, and during one heist, he impressed a young super at the bank so much, the kid promptly chased after him! They tried teaming up for a bit, as both had earth powers, but Geode's inexperience hampered Tellurian so much that the guy finally left the kid on the scene for the cops to pick up. They reconciled a few years later, but they never teamed up again.
Mr. Big and Pyrepower - c'est moi! I've been helping Pyrepower out on and off for several years. She's a lot younger than me, and she runs with her own crew most of the time. I've been mentoring her (and that's all, you fanfiction weirdos) because I see a lot of potential. For my part, I've got enough material wealth to do what I want, so these days I mostly goof around. None of her capers are going to threaten what I want, and nothing I'm doing is going to get in her way, so it works out.