Orlando Figes has demonstrated pretty conclusively that Stolypin's reforms were a failure even while he was still alive. This was partly the result of his own personality (he did not know how, or could not be bothered to form coalitions within the government, so remained very isolated and dependent on the tsar's favor), but mainly due to the peasantry's reluctance to leave the communal system.
It cannot be said that Stolypin's reforms failed because of his personality alone. Stolypin had to fight against opposition from the right and left factions. Much of the nobility failed to understand Stolypin's reform program. Those from the right were desperate to retain their personal privileges, even if it meant retention of autocratic rule at all costs. They feared that the "old order" would be undermined. While those on the left prefered that the land was to be consolidated - involving whole villages, rather than allowing for dispararte parcels of land. Stolypin's most serious opponent was Nikolai, who resisted any changes which affected his perception of autocratic rule.
Granted that Stolypin was uncompromising, but this is a trait coming from an individual who believed he was right. He was fully aware that he was dealing with a nation undergoing considerable internal social and industrial changes. Such new economic ideals emerging in Western Europe during the late 19th and early 20th century proved incompatible with Russia of the old.
Stolypin's tenureship as Prime Minister has been considered by Figes to be a failure. Yet it must be realized that Stolypin, achieved a number of positive things for Russia. He restored order over the revolutionaries after the 1905/6 turmoils. The fact that he was able to introduce agrarian reforms by increasing productivity and agricultural efficiency cannot be ignored. What was wrong with allowing the peasant who were free to choose, to own land if they desired, a new concept in creating a new class of land owners, and for the establishment a special loans bank to support their financial needs? This was a huge progressive achievement in the light of what I alluded to earlier. Furthermore he extended zemstvos and promoted education and introduced insurance for workers. To undermine or ignore these achievements as inconsequential is grossly misguided.
Present leftist 'wisdom' claims that Stolypin's assasination had no effect on Russia's development. I would contend that had there been more faith and understanding of Stolypin's reforms, and had there been internal stability then there would have been an excellent opportunity for Stolypin's reforms to be fully realized.
To blame the lack of success of Stolypin's policies on his personality alone ignores the temperament of Russia, and the "will" of its Emperor. Stolypin may have failed to solve the problems, but at least he can be accredited for singularily trying to do so.
One side would tender that Stolypin's reforms were regressive, while the other side would support the notion that his policies were unusually progressive.
One's personal interpretation of this question really comes down to which ideological position is prefered, don't you think?