When we put up the roles a few years back (the new stuff this time is the top part through starting scenarios), the idea was to get some basic structured options into the game where it was totally lacking (and still is), but there's some stuff buried in the dev page that should help over the longer term. For instance with the Hero role, we stuck villains at the top with stuff like "evil plots" so that there'd be a larger direction, sometimes peeled in layers (the idea behind the interrogation stuff) -- granted that isn't even started yet -- and I think the dullness of repeat megabeast slaying will be alleviated somewhat once they are an actual post-worldgen actor with better-defined relationships with surrounding communities. In those terms, the Slayer of Night Creatures role section "torment the living" is more explicit and overall they're supposed to provide some circumstances that could chain together into a bit of character arc for yourself (especially through the curses and exposure section). I guess this goes with "making history deeper so you care" from the OP. That all relies on clear exposition and the player being able to decide what's important, and we can see what that's like done piecemeal and badly in the current version of the game (with the site invasions for example, or most anything else).
All of the roles weren't intended to be drive a traditional story, though -- I think for us, Hero and Slayer of Night Creatures were set up along those lines, while Treasure Hunter and Explorer were more for recapturing a sense of discovery (with some history thrown in), and the Thief and Trader were directed at framework considerations (crime/justice and economy). The starting scenarios are going to jump ahead a bit on framework now.
It'll take a while for gaining money to be a worthwhile goal -- blowing your hard-won spoils on fast living (as you might be inclined to do in real life) isn't generally satisfying in a computer game, where there's little incentive or player enjoyment associated with leisure spending. In one of our experimental projects, we toyed around with "debauchery", "high life" and several other counters that'd reward you for behaving or spending money in certain ways, and that does work to some extent to give the game more structure and almost an expeditionary feel. That approach will probably be tested in DF with our new taverns, though it's somewhat harder to determine the reward (in the experiment, there was a stamina analog to adjust, but we'll have to be careful not to be as gamey). There'll be all sorts of places where hoards of player money can be leveraged eventually, but it'll require the economy to grow up to the point where armies have to be provisioned and so on. Money could also corrupt any piece of the justice system we add, once the individual links are in place. Thinking of how we'd even begin to set that kind of thing up was part of the motivator for the latest addition of the framework for the starting scenarios section. It would have been possible to finish the caravan-style economic supply-demand stuff earlier, but I'll be happier having law, property and status as better encoded concepts as a foundation for the economy and justice system.
Reputation-wise, we've sort of built a mess to extract ourselves from -- there are rumors stored everywhere that give rise to reputations with certain people and groups, and older group rumors get converted into a reputation with a group where the cause isn't remembered as precisely. Having it spread all over the place makes it hard to just hang your hat on, though. A basic reputation summary in your info screen might help, and further reputation effects (some are listed in the Hero role rep section). There's also the more objective historical legend you are building up, which you might have access to in some way.
The main difficulty of status-based approaches to player reward is just the amount of command options that'd need to be in place to make holding a position worthwhile or realistic -- and all of the command options need to be backed up by mechanics (which we are sorely lacking for our site-to-site struggles). Similar with the properties for sale -- it's a large reward, but it's also kind of a static end point unless you can get some use out of it (meaningful storage, defense, subordinate work area, collateral, citizenship options etc.). Artifact quests/rewards/etc. are easier to make fun, and we're going to be trying them out pretty soon in adventure mode.
So yeah, I wholeheartedly agree with the overall aim here and I think we're pointing toward it. The state of the current adventure mode certainly gives one pause, but I think there's some hope even in the roles.