Hey zenkix. Your problem is that you’re thinking too small. Being down $500 after 4 sessions is no indication of anything. You need to look at the whole picture after a much longer period, such as 3 months+ to have some idea. I assume the buy in is max $200, so really you’re down 2.5 buy in’s…that’s nothing.
I also usually bring only 2-3 buy in’s, because if you’re stuck that much, any subsequent buy in’s you’ll just think about recouping loss which is not optimal play. I prefer to call it a day then and come back another day with a fresh head.
The best way for you to play is to set aside a number of buy in’s. For live casino play, where the games are fairly fishy, 10-15 buy in’s is sufficient. So if the max buyin is $200, set aside a theoretical 2-2.5k. Then keep a record of each session you play, the number of hours, and the profit or loss. Also remember key hands, key mistakes, note them and what you should have done differently. Don’t look at it as a series of single sessions, but as one loooong session. Losing 2 buy in’s in one day doesn’t necessarily mean you suck, but being down 10 buy in’s over a month play might.
To your other points. Raise or bet for one of two purposes. To get your opponent to fold a better hand, or to get them to call you with a worse hand. In live poker, most of them time you’re trying to get them to call with worse, as they hate to fold better hands and will most likely call you down with top pair or better. Really, it comes down to a lot of factors and experience. Don’t get into the habit of betting when they can only call you with a better hand, and will always fold with worse hands. For example, say opponent raises preflop and only does so with 10 10+, AQ+, and you call with 99. The flop comes Q 4 2, opponent checks, and you think he probably missed completely. Should you bet? There are you hands you beat that he can call you with (unless he sucks), and he calls with hands that all dominate you.
As for playing with scared money…don’t. Teach yourself not to, and set aside a balance of poker money and only poker money. Money is just for keeping score.
For chasing outs, mutiply the outs by 2 for the odds with one card to come, and by 4 for 2 cards to come. So with 15 clean outs, and turna nd river to come your odds are 60% (actually closer to 54%). The rule of 2 and 4 is an approximation. If you’re sure you have 15 outs, get it call in on the flop. The problem people have is they estimate their equity with 2 cards to come, then pay way too much to see just one card. Say you have a 30% chance to make the nut flush, the pot is $45, and he bets $30. Looks good right? Calling $30 to win $75 with a 1/3 chance? Your odds of hitting on the turn is actually only about 17%. You miss. The pot is now $105, he bets $70. Again the price is too high.
Then implied odds comes into it. Can I pay too much for the turn card, knowing that if I hit my straight he’ll have no idea and I’ll take his chips on the river? This rarely applies to flush draws as everybody looks for them, but more for chasing your combo draws and two pair draws.
Ok that’s a lot of information and I probably rambled a bit. Hope it helps.