This is a tough question. You need to take into consideration that a Wedding is (hopefully) a "once-in-a-lifetime" event. You have only one chance to get it right. A school may book you once, then give you a second chance, but you don't have that option at weddings.
How well do you know all formats of music? At weddings you play for people 8 - 80. If someone wants a foxtrot or a waltz, do you know what will work? Do you know what works best for Motown, disco, big band, or funk?
How confident and clear are you on the mic? Do you have a wedding planner? You might want to invest yourself into a public speaking course. Additionally, you may want to ask assistance from someone in your local DJ association who is already excelling in the wedding market. They won't tell you all their tricks, but could help with your planning portion.
Weddings have a format and most clients will turn to the DJ for the sequence of events. If you don't know the format/sequence, you could be leading a couple into a bad reception.
You may even want to ask another DJ in the local association if you can 'tag-along' and learn. Remember to wear your tux, observe, and take notes.
How long until you are ready? Only you will know that. You may find someone with a VERY flexible agenda and expectations on their wedding day. You don't want to screw up a $20,000 wedding day (nor do you want to do the same for a $5,000 wedding day, but a flexible client may understand some of your slip-ups).
Brian
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