Help with a character D&D 3.5

[Rainbaw]

I'm doing a new campaign (i'm the DM) and one of my players went with a Urban Ranger (unearthed Arcana) so now they are at level 2, he came to me asking to read trough books together and find something fun to do, PRC, other classes, feats and even items to use.
We came down to a StreetFighter (complete adventurer), The requeriments for this class are Combat expertise and improved faint, +6 Base Attack and 5 ranks in three specific skills (local knowledge, gather information and intiidation i think).

So, we came down with some multiclassing since a ranger 15/SF 5 would end not beign what he wanted to do in the first place.
My solution was this Ranger 4/ Figther 4/ Rogue 5/ Streetfigther 5.

Leaving 2 levels open for anything else, in case we do it all the way to 20 and he would have the PRC by level 8. We came with a progression in the classes that would leave him witouth XP penalizations (he's playing a human).
As for feats, he would take combat expertise, improved faint, improved trip and probably improved disarm. I can remember a feat allowing a character to use weapons of a bigger size, and maybe he can use that one. And the feat to use an exotic weapon.
For weapon he's going for a spiked chain, lets him dissarm and trip peole with a decent reach. if he gets a big one it would deal 2D6 instead of 2D4 (and i'm not sure if the size affects the reach.

The strat would be the caster of the group enlarge him as soon as he learns that spell, making his reach of 20ft, he can trip, disarm and attack people at 4 squares, if he trips someone and then attacks he would get the sneak attack from rogue and the PRC.

Any suggestions on how to improve this character over the time? he will keep using light armor and maybe get a medium one made of mitrhil. I can't think of any other feat he could use or a better weapon. Or any feats nor even PRCS he could use instead...

What he wants is a melee-mid range character, that can stand a beating but still move lightly (so no heavy armor). We decided on rogue mostly because tripping someone would make an automatic sneak attack. Warrior for the feats and the armor proficency, ranger mostly because he already is a ranger and didn't want to re introduce himself so early on.
WEll i appreciate that you did actually read all that, thanks! i'd love any suggestion or criticism.
And sorry for my poor grammar, english is not my native language

[Xerlith]

Leaving 2 levels open for anything else, in case we do it all the way to 20 and he would have the PRC by level 8. We came with a progression in the classes that would leave him witouth XP penalizations (he's playing a human).
As for feats, he would take combat expertise, improved faint, improved trip and probably improved disarm. I can remember a feat allowing a character to use weapons of a bigger size, and maybe he can use that one. And the feat to use an exotic weapon.
For weapon he's going for a spiked chain, lets him dissarm and trip peole with a decent reach. if he gets a big one it would deal 2D6 instead of 2D4 (and i'm not sure if the size affects the reach.

Well:
1. Whatever have your players done to you that you play with the multiclass XP penalty rules?
2. Improved disarm? What for? You can use the action to just kill the mook...
3. Size of the weapon does NOT affect reach. Also 2d4 is 5dmg on average. 2d6 is 7dmg on average. A feat for 2 points of damage? Thanks, but no thanks.

Finally - drop the Streetfighter class. 4 levels of rogue + the Improved Initiative feat do everything that class does - and do it better.
For Improved Trip without the Combat Expertise feat tax grab two Barbarian levels - Spirit Lion Wolf Totem Whirling Frenzy Barbarian. Pounce, Imp. Trip, Frenzy gives an additional attack.

I figure the character's DEX focused - if so, I'd recommend grabbing two levels of Swordsage for Assassin's Stance and the Shadow Blade feat (The stance gives 2d6 Sneak Attack damage, the feat gives dex to damage, Swordsage gives melee goodness and a bonus to initiative) at higher levels.
Something around... Ranger2/Fighter2/Rogue4/Swordsage2 or Ranger2/Rogue4/Barb2/Swordsage2 I guess.

What is the Ranger's chosen combat style?

[HammeredWharf]

We decided on rogue mostly because tripping someone would make an automatic sneak attack.

No, that's not true. Specific conditions have to be fulfilled for Sneak Attack to work. Being prone isn't one of them. Tripping it still nice, though.

I'd also recommend a Tome of Battle class, if you have access to them. Warblade and Swordsage both work with the "thug" archetype you seem to be going for, with some refluffing.

[Telonius]

My first suggestion would be to take a heavy black marker, and blot out the "XP for Multiclass Characters" section on page 60 of the PHB. It doesn't add anything fun to the game, it penalizes already-weak classes, and it makes it more difficult to build the sort of character a player wants to play (as you've seen). It's a horrible, horrible rule. (I'd recommend cutting out the section and burning it, but iirc there's something important on the back side of the page).

[zingbobco000]

Well:
1. Whatever have your players done to you that you play with the multiclass XP penalty rules?
2. Improved disarm? What for? You can use the action to just kill the mook...
3. Size of the weapon does NOT affect reach. Also 2d4 is 5dmg on average. 2d6 is 7dmg on average. A feat for 2 points of damage? Thanks, but no thanks.

Finally - drop the Streetfighter class. 4 levels of rogue + the Improved Initiative feat do everything that class does - and do it better.
For Improved Trip without the Combat Expertise feat tax grab two Barbarian levels - Spirit Lion Wolf Totem Whirling Frenzy Barbarian. Pounce, Imp. Trip, Frenzy gives an additional attack.

I figure the character's DEX focused - if so, I'd recommend grabbing two levels of Swordsage for Assassin's Stance and the Shadow Blade feat (The stance gives 2d6 Sneak Attack damage, the feat gives dex to damage, Swordsage gives melee goodness and a bonus to initiative) at higher levels.
Something around... Ranger2/Fighter2/Rogue4/Swordsage2 or Ranger2/Rogue4/Barb2/Swordsage2 I guess.

What is the Ranger's chosen combat style?

Spiked chain is totally worth it. What you should have said was: A feat for two less damage, two light weapons (ranger-ness), trip, disarm with a +2 bonus, and reach and you can use it against an adjacent foe, so it's better than most reach weapons. 1 feat for all that? Totally worth it. I agree with your streetfighter opinion though, it's actually probobly worse than rogue. Drop that for the template, red dragonspawn from the revised bestiary of Kyrnn. +3 LA for: +8 STR, +2 DEX, +6 CON, +2 INT, +2 WIS, and +4 CHA. If you use the LA buyoff version you will finish at level 18. Other than that take a couple levels of sorcerer (as you already have a level in it) for nice spells that could increase your combat capacity. I.E. Haste, Blur, Fist of Stone etc...