You pays your money and you takes your chance. Compared to what the German airborne forces pulled off in Holland in 1940, this one looks downright reasonable. On the one side we have the German front-line units, badly depleted and severely short of supplies, trying to hold back a concentrated armoured thrust, on the other we have ad-hoc and reserve German forces trying to mount an offensive against elite airborne formations who only have to hold on to win. And the Allies have air supremacy and lots of bombers.
That said, I still don't like it. The problem is the narrowness of the advance - basically a single road. It's not just the chance of a bridge being blown - if the Germans get a solid block in place anywhere on the road between Eindhoven and Arnhem the whole plan falls apart. A fast armoured breakthrough is best conducted by pressing on multiple axes, finding a weak spot, then busting through and exploiting, but here there are just too many chokepoints to make that viable, so you're reduced to playing sledgehammer. Plus the added risk of counterattacks against your very thin supply corridor, after the spearheads have passed.
Which brings up another point - to work, the plan
really needs a Patton or Rommel leading the armoured column, screaming that logistics is for losers and his flanks are someone else's problem. Instead, it would get Montgomery and his team, and for all their undoubted abilities, none of them are hell-for-leather stormtroopers. I can easily see them pausing at point A for reconnaissance, then pausing at point B to let the support units catch up, then pausing at point C to rotate depleted units off point, then arriving at point D to find their chances of success have evaporated. And, as
@Carl Schwamberger has pointed out, the outline plan they came up with was over-complicated and bizarrely cautious.
On top of that, I think the gains from a successful Market-Garden have been over-sold. Suppose it all works and XXX Corps gets a bridgehead over the Lower Rhine. It's now October, XXX Corps is fought out, its supply line is a single road and Antwerp hasn't been cleared behind them. By the time the Allies have sorted out their supplies and can consider a breakout, the Germans have had time to reposition, winter is coming on - and the winter of 1944-5 was a hard one. The most likely outcome is static fighting around the bridgehead, with the breakout not being achieved until February-March. Sure, it'll forestall
Wacht am Rhein - but since the main practical effect of that was to eliminate the Germans' last aircraft and armour reserves, I'm not so sure it's a gain.
The German gamble at Dordrecht in 1940 was worth it because success put them inside Fortress Holland, leading to Dutch resistance collapsing in a matter of days. Success in Market-Garden puts the Allies in Arnhem - which is a nice strategic position, but still a long way from the Ruhr or Hamburg or anywhere really critical. It won't end the war by Christmas.