I just finished playing LtH for the first time (Joyless, not on Pain mode), and I absolutely loved it. From the moment the game started, it felt like I was playing an actual Lisa game, not just a fangame.
The main character (Beltboy) is an interesting take on a Lisa protagonist. Whereas characters like Lisa, Brad, and Buddy were already more or less 'broken' and psychopathic at the game's start, Beltboy legitimately cares about his friends and has something of a sense of morality, which makes him much easier to identify with (although this IS Olathe, so those morals only go so far).
The relationships between the characters felt genuine and well thought out. There are three main characters (the definitive edition adds other routes/characters but I only played the base one), and each of them has a strong personality and a tangible relationship with each other.
If I had to nitpick, some of the bosses felt like they took way too long to kill (to the point where I was wondering if I was doing something wrong), and it felt like there were a lot of areas where it was *mandatory* that I drop from heights where I would take damage (this is especially prevalent in the 'mushroom trip' section). Also, there were a few too many enemies I had to fight right before the final boss, which kind of ruined the flow a bit. But still, those are nitpicks.
The presentation is amazing; every area, character sprite, and line of dialogue felt like something right out of The Painful or The Joyful. Somebody could have told me that Dingaling made this game as a canonical sequel and I would have believed it. The story is so well integrated into the world without being reliant on the previous games that I honestly consider it to be canon.
The different rival gangs were so well-designed! I'm just gushing at this point, but I think it's worth going into detail: I wish Dingaling had put this much effort into all the different gangs in the main series. Every gang in Hopeful had a unique quirk and was relevant to the story at some point or another. It wasn't like Joyful where a lot of them were just sort of there for the sake of existing without any sort of depth or context (I'm looking at you, Dice Mahone and Hawk Hollywood). In Hopeful, every single gang had their own design, quirks, goals, and even personality. The Engine Enthusiasts were brutal but honest and wanted to collect and maintain cars. The Sportsters were idiots who wanted to keep playing and watching 'sports' but forgot how they actually worked. The Kegger Crew were a bunch of pissed off redneck drunks who could actually be quite friendly at times. Again, I'm just gushing, but I think the different gangs was one of the best parts of the game.
If anybody is playing for the first time, my advice is to buy as many HP/SP recovery items as possible in the mid-to-late game. You will probably get as much perfume and weapons/armor as you need just by exploring and defeating bosses, but ways to heal are always at a premium.
Thank you so much, taco salad, for making this incredible game!