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So how is 'Cheering for Wallets' and 'Best Bank Account Wins' better than 'Shrewdest Management Wins'?  That's essentially what you have in the NFL, where stability and skill in management and coaching (Steelers, Patriots) defines who the perennial winners are.
The battles of baseball are like life.  The playing field for everything - jobs, sales, market share, an apartment - is not level.  Your business competitor has a trust fund and deeper pockets than you.  The other person being considered for promotion went to a more expensive school.  The other people applying for that apartment know the owner's son.  And so on.
And the funny thing, in baseball and in life, is that while the odds may be stacked against the underdog, the underdog wins a surprising amount of the time.  Because other factors ultimately are more important than starting capital.
The roto analogy is not a very apt one, I think.  Mainly because of the draft; teams like the Yankees and Red Sox rarely have access to the young and cheap years of talents like Strasburg, and Harper, ARod, et.al.  And for that matter, while I don't play roto, I imagine a league where there was a range of starting dollar figures from $360 to $720 would be pretty interesting.
To each their own, of course.  I prefer competition and economies that are as real as practical.  Sure we don't want AA caliber teams playing all-star teams, the kind of disparity you'd start getting if the payroll inequities became too great.  So I support the general way the draft is structured, and the luxury tax, and things of that nature.