I'm gonna help you out with a secret for the cash play. The money is a way to keep score. Only in the beginning of gambling. The money you put up... consider it gone. Don't even think about it. Also, only play players lesser than you in the beginning. Not even people that play even with you. Just in the beginning until you get used to it.
There are guys that will drill me for $5 a game, for $200 a game need the seven. It will only come with experience.
When gambling, you have to take the guy out of his element. If he likes 9 foot tables, play on the barbox. If he's used to ten dollar sets, save up and make him bet fifty.
****Remember this. The only difference between the lower tier pros and a lot of local really good shortstops playing for $1000, is that the pro does it every other day. Same thing for the $20 dollar set. You see these every day, right. It becomes second nature. When you get this down, try the $50. Get this down, try $100. So on. So on.
Some people, and you know who you are, have the burn to win. They have the F%#$ you. F%#$ you. I won't let you win. That attitude is seen in all good players. There are also guys that just like to be seen gambling, and lose quite frequently. They don't care. They just want to be part of the scene. You need to find out early which one you are. If you're the latter, stick to playing locally and cheap. A lot of matches come down to who has the most desire.
Nothing beats time on the table and experience. So, jump in the pit and get your feet wet. You can develop the FU attitude. I promise. But, know your limitations. I don't play Johnny's speed. I am realistic about my place in the billiard community. You will too.
Good Luck, The Craw.