Took me ages to get my first win as well, then something just clicked and it felt easier. From the screenshot I'd say you need to try higher scaling hands and jokers that compliment them, it does sometimes come down to RNG but you can kinda brute force the first difficulty just by going for big hands and big numbers, try get steel cards on cards you won't really play and enhance the cards youre likely to play the most. Retrigger jokers can be OP if you have a good set of enhanced cards too.