I think that if we gamble regularly, the more knowledge and experience we have in gambling, our winning rate will increase.
Purely depends on what gambling game you're playing. I don't think it would make much of difference to a pure-luck based games like dice, roulette, and anything similar. For sports betting, experience and knowledge may have a slight advantage but the odds would make things a little complicated and challenging for you to decide where to place a bet.
Well, I can't be sympathetic towards a gambler who losses everything, because first of all they have already made a choice and those are just to consequences for what they have done recklessly.
If we play games based on luck, it will not increase our insight or knowledge and bring us closer to luck, but it will make us addicted to gambling and this can cause losses. So we must be able to limit ourselves from gambling too much in terms of the more we gamble the closer we will get to it luckily that would be very wrong. However, if you gamble based on skill, it can increase our insight in analyzing bets and get closer to luck and indeed this can be a challenge for us in betting because if we make the slightest mistake in analyzing bets, it can cause us to lose.
We don't need to be sympathetic to people who gamble recklessly because it is their own fault that they gamble excessively. Even they lose a lot of money and feel they should be pitied, but it still can't change their situation for the better, but it can be a lesson for us gamblers not to overdo it in gambling which causes big losses.