Just Recently, I decided to replay through this game once again just to see if my opinion on it has changed after reading all the comments on this forum and a couple of my opinions have changed:
1) I will be the first to agree that the game was very much ahead of it's time and that a lot of things in games now a days can be said to have been inspired from this game, however, I still feel that game didnt' execute it as well as it should of.
2) The game actual takes a lot less skill then I thought it did originally. The best stratagy to beat the enemy is to just rush up on them and constantly kick them or throw them as they try to get up, which allows them to not even get a hit on you. That being said, the enemy can do the same thing to you, which I guess if far, but I feel it makes this game into a sprint to see who can know who down first, which isn't exactly a great idea for combat, espically for a Beat'm-Up.
3) I actually kind of dig the soundtrack

. My favorite is the main theme that plays as you explore the world, as it's rather up beat and makes the grind kind of bareable... just a little though

.
4) The only power up needed to rip the game a new one is Dragon's Feet... NUFF SAID!
So yeah, I guess I still didn't like the game, even on the second playthrough. Now before you go all crazy on me and tell me that I should be easier on it for being an older game, hear me out:
Another game that decided to fallow a style very similar to River City Ransom was Zelda II. I know a good amount of people don't like game for things like an crazy save and lives system as well as the amount of grinding, but Zelda II has a solid 5 elements it had done better the RCR did (I will not include story because that just isn't far):
1) It used a level up system that was simple and made sense, along with allowing the player to decided on what stat he wanted to devote himself to. It takes out the exparamentation and the randomness of wasting money on random food that you might not gain anything from.
2) Zelda II's combat is just better. I would say Zelda II's combat is more like a Beat'm Up then River City Ransom is, and even though the combat is hard, it's a lot more engaging then simiply mashing the kick button until something dies or rushing the boss and kicking them while they are down. To simply put it, Zelda II's combat is engaging and fun where RCR is Repetative and Boring. Plus, when you die in Zelda II, most of the time, it's because you didn't prepare yourself well enough for the encounter you where about to come across, where RCR has you die because you got cheap shotted for once. Also on the note of dieing, at least when you die in Zelda 2, you know that after your 3 lives it's game over, and BOSSES DON'T REAPPEAR AFTER YOU HAVE GOTTEN A GAME OVER (Yeah I still am upset about that)!!!
3) Despite the fact both games are rather Grind Heavy, Zelda II is actually much less grind heavy then RCR, and this is why: Zelda 2 is a large adventure that is supossed to take multipule sit downs and the game never forces you to grind. If you just fight every fight you encounter and do every daungon, as long as you know what to do on certian enemys, you actually don't need to grind at all. RCR on the other hand is a very short game that can be beaten in under 15 minutes if you know what you are doing and are at max level, the problem is the game takes forever to get even high enough to take that time to get that high. It's just a pain really...
4) Bosses are really inconsistant and aren't very impressive. In Zelda II, bosses are big and very different from the enemies you fought in the game. In fact, even a good chunck of the enemies are vastly different from on another, but this game just has the same type of fighter for everything, except maybe with a certian type of enemy being smarter, stronger, or come in a group of two. It's just not very impressive and as long as you nail the first hit on the bosses and knock them down before you get knocked down, they are pretty big pushovers.
5) That last and more important factor, I feel Zelda II has actually aged a lot better then RCR. I mean, yes, the save system and lives system is terrible, but everything else about the game works well in to context of the way games are today. The game is challanging and would make for a intersting remake if Nintendo decided to freshen up issues like the save system and get ride of the lives, and bring it up to snuff as a 3D Classics title like they did with Excite Bike, but they won't.
RCR just doesn't hold up very well in today's standards and with issues like gameplay flaws and a desprate attampt at extending it's gameplay time, it just makes the package feel it's trying to do to many things. I mean, the things it's trying to do are great, but it's doing them without thinking them through, and thus makes the things not very good. I feel if it got a nice remake and updated everything, the game could be very good and maybe if I had played it back when it first came out, I might of liked it more and looked at this playthrough as a trip down nostalgia lane, but as I always say, nostalgia sometimes blinds the truth and the truth is, there are better games that does what RCR tried to do better...