You need to be clear in your own mind what you want to achieve by any particular bet. You might want merely to stay in the hand to look at the flop or the turn or river; you may want to build the pot, because you think you have the best hand or are likely to have the best hand at the end. You may want to make a bet to test the reaction of an opponent to try to gauge what he has in his hand; you may want to frighten players out of the action and win the pot there and then.
If you do want to win the pot there and then, the ultimate pressure bet is to go all-in (bet all the chips in front of you). You are unlikely to be called and will win whatever is in the pot already 95 per cent of the time. However, you may get called by a very strong hand, and then you may lose all your money. Generally however, the more you raise, the more you are trying to win immediately. If you raise modestly, you are more likely trying to build the pot because you have the best hand at that moment, or think you will in due course.
A modest pre-flop raise would be two or three times the Big Blind. A medium size raise would be four or five times the Big Blind. A seriously big raise would be more than that.
Post-flop, to bet half the value of the pot, or the whole value of the pot are both standard moves with what you believe to be the best hand at that moment.
Important Note: when I say, “if you feel you have the best hand” that will be a judgment that you, and only you, can make. You will base your decision on a number of factors: you may definitely hold the nuts at this moment; you may have top Pair with top kicker - or 2 Pair, or Trips with a Pair in the hole - and realize that it is very unlikely anyone has you beaten; you may just sense from the other players’ demeanour that they have nothing and that your hand is probably winning; you may decide to run a complete bluff because you think no one has anything. You may be wrong. To begin with, you’ll be wrong quite often. But, you must form a judgment and then act accordingly. Only poker experience hones this judgment and, having accrued enough experience, then good reading and good practice will turn you from a beginner to an average player and then on, possibly, to the poker heights.
In terms of gauging your raise, simply, the higher you bet, the keener you are to win the pot there and then and not risk being overtaken by opponents when the community cards appear.

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