I've done tons of trades over the years. I've done some great trades with people I didn't know beforehand, but the best ones are with long-time friends. Those are great because you've been helping each other out with stuff for years so I never feel like I need to be sure I'm getting an exactly even deal. Close is good enough because it will all even out in the long run. These trades also tend to come together quickly and easily.
Some advice I would give:
1. Make sure you feel comfortable with what you're giving up. For me I've always been able to differentiate pretty easily between something I would miss dearly, and something I wouldn't lose sleep over because of what I'm getting in return. If you're not sure, maybe hold off on doing the trade. If you know you have trouble letting stuff go, maybe trading isn't for you.
2. If you're making a trade with someone you don't know, make sure you feel 100% comfortable before sending your cards. Ask for references and check them. If the other person has a long term reputation and you don't, you should probably send first. And if you have the more established reputation, you can ask your trading partner to send first. If they balk at the idea, maybe you dodged a bullet. You can also send the trade in stages. If you're each trading 5 cards that are valued at $500 each, there's no reason you couldn't mail one card at a time so that you both aren't worried about losing all 5 cards at once.
3. For me the best experiences with trading and deals have always come with friends. So with that in mind, try to make some hobby friends. Put yourself out there a little bit, provide some value to people. If you're knowledgeable about a certain area of collecting, share with people, answer questions etc. Then keep an eye out for who returns the favor.
Some favorites that came in trades with other net54 members:
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