This column has been generally positive about Barack Obama’s re-election prospects, but on the eve of the GOP convention (assuming it is not hurricaned away) a few major caveats lie on the road ahead. Caveats that could hand the election to Mitt Romney & Co.

First and foremost is a growing money gap. Obama acknowledges he may be the first incumbent president in history to be outspent by a challenger. Thanks go mainly to the Supreme Court’s Citizens United decision that literally abolished any limits on campaign contributions through various entities—notably the “Super PACs,” to which billionaires have already given many millions to those associated with the GOP. Total Republican fundraising may exceed $1.2 billion.

The Democrats have not fared nearly so well with Super PACs, though direct contributions to the Obama campaign and Democratic National Committee have held up fairly well. Still, due to Obama’s personal distaste for the care and feeding of liberal high rollers, many big-time givers such as billionaire George Soros are on the sidelines.

Enough money used the right way against Obama, whose total dollars may lag the GOP’s by 15 or more percent, could refocus the campaign on the fragile economy and high unemployment to change the game by October. There may, however, be a saturation point where excess dollars do little more good. But we’ve never had a situation where a seemingly unending river of cash flows to one side.

The other big worry is the various voter suppression/limitation laws and directives in at least three key states—Florida, Ohio and Pennsylvania—which could tip any or all to Romney. Obama basically needs two out of those three to win—though there may be a far more difficult path to Electoral College victory.

Between voter purges, draconian voter identification laws and severe cutbacks in early voting days and hours, all admittedly aimed at minorities and the Democratic base, tens of thousands of prospective Obama voters may be deprived of the franchise in those three essential states where he currently clings to small leads. Welcome to the 1950s.

It is still possible the courts will intervene and find some or all of those actions in violation of federal voting or civil rights laws. Also, massive, on-the-ground efforts to help the elderly and minorities obtain proper ID, inform them of the newly restrictive hours and actually get them to the polls is under way in those states. The task, however, is Herculean if not Sisyphean, charting new territory. We don’t know yet if it will be sufficient to compensate for the potential loss of those tens of thousands of Democrats.

There is also the prospect of worsening economic and jobs numbers. This is one area where Romney clearly leads, although his unlikeability and widespread disgust with a GOP too far right on Medicare and social issues is a severe counterweight that could yet bring him down.

There will be two conventions and three debates to further scramble the numbers. So be concerned, Democrats, but neither worry nor rejoice about the polls until late September.

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Don Rose is a regular columnist for the Chicago Daily Observer
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