The game is tough, but Ryan is making it look way harder than it is. He has Khalid, Jaheira, Xzar and Montaron in his party, all of whom will have told him to travel south. In fact they repeatedly bitch at you to do so and eventually leave your party if you don't - it's the closest the game gets to a HUD symbol saying 'FOLLOW'. The fact that Nashkel, to the south, is worth investigating is mentioned by many NPCs and should be in the journal also (although from the looks of it the journal has been redesiged and maybe some detail has been lost).
Ignoring this, Ryan goes east, then north, into maps that would be very tough for him even if he was well-prepared and putting a lot of thought into his decisions. He clearly isn't well-prepared or thinking very hard; anyone who cares enough about the game to guess the difference between 'mages', 'thieves' and 'fighters' will know that it's probably not a good idea to have mages and thieves charge in with melee weapons at the head of your party. Ryan also has three fighters in his party capable of tanking decently, not just one - since Jaheira and Montaron are multiclass fighters - but that doesn't matter since he has them in horrible armour, using weapons they are no good with.
Anyone who thinks this game looks ridiculously tough should at least realise all the basic stuff Ryan is screwing up without appearing to give a shit. Also as someone has already mentioned, equipment comparison is barely even a factor in these games. If your guy is good with longswords, you give him a longsword. Then you forget about it until you find a longsword +1. Then +2. If you find the 5 types of armour confusing, check their price values in a shop. Splint mail is like 100gp, plate mail is 600gp, and full plate is like 2000gp - or something along those lines, anyway. That should tell you literally everything you need to know.