Gambling regularly will make a person addicted into it. If you keep doing a work daily then after sometime his conscious mind accept this fact and build a mentality base on these facts which will directly/indirectly command your mind to continue that things daily even in upcoming days. Thus it turns into a strong habit and you have to suffer whenever you want to get out of it. And when you found that you don't have enough money for gambling but as you already decided & build such mentality to gambling regularly, then And will be in troubles. Even there will be chance to involve yourself in unusual activities because of managing money for gambling. So it will be better not to gambling Daily
I agree, gambling is already dangerous but it is more dangerous for those who gamble every day. As you said, if you find out that you don't have enough money, if you continue your gambling habit, there is a big chance that you will find another way to gamble more, you can borrow money from a friend or take a loan, steal, sell the properties etc. And the ending is that you will be in debt and you will not be able to pay back what you borrowed because of your addiction to gambling. I know someone like this and his got to the point where he sold two cars just to have more gambling wtf.
There is a big chance that you will become addicted to gambling if you gamble every day, even if we say that you are in control, but if you gamble every day, it is still dangerous for you. So it's better to reduce the time spent on gambling because it's really bad for gamblers. I also gamble once in a while and it's okay, I win at least a little bit.