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I'm no expert, but just to get the ball rolling, table per table, online play is harder. In fact, in trying to compare stakes, which is not a reliable science, many players have suggested the ratio is 10 to 1. In other words, if you are a successful $5/$10 ($1000) NL live player, then you would likely best fit into a $0.5/$1 ($100) online game. Again, these are just estimates and there's no exact way to correlate, but it's definitely something to keep in mind.
Live players are generally much weaker, easier to read (polarized ranges), and don't like to fold (showdown monkeys). Online players are overall better, harder to read (no physical tells), and by comparison will fold more often. When playing online, you want to take advantage of all the things you can't take advantage of live - multi-tabling, using a HUD, taking good notes, and table selection.
If someone is a reasonable winner @ $5/$10 ($1000) live, but has never played online. My suggestion would be to deposit $1000 to a site and start playing $25NL. That player should be able to crush the games while getting used to all the new online game variables and then naturally work up the stakes. If he or she gets off to a slow start, don't be ashamed to drop down to $10NL if the bankroll hits $750 or so. Although the game of poker doesn't change, live play IS different than online play.
Also, bankroll management shouldn't really change from live to online, but error to the side of caution with your online bankroll as money can virtually come and go quicker and is harder to deposit and withdraw compared to live.
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