Are you positing a particular model of the good life here?
One weakness with distributism, I would argue, is that Chesterton et al sometimes seem to suppose that the common man generally only has one set of interests or desires, and distributism can satisfy them. One of Chesterton's general problems, actually, is that while he says a great deal about ordinary people, he often seems to be substituting his picture of what an ordinary person is like for what they really are like. In the real world, though, we notice that people tend to disagree about what the good life is, and they often have conflicting ambitions.
So one argument against the three-acres-and-a-cow model is that you'll just get people who don't particularly want to live in a quaint little farming cottage (or whatever your distributist equivalent is), and so they sell this private property in order to do something else. Maybe you sell your three acres of land to a big farming collective, get yourself a little apartment in the city instead, and invest the rest of the profits in your lifelong dream of becoming an artist or investing in the stock market or founding an import business or becoming a politician or whatever else you might be into. A certain proportion of people are likely to do this, and over time big capital firms are likely to evolve again. If everyone wanted to live G. K. Chesterton's imagined rural idyll, that might work, but most people don't. Arguably even Chesterton didn't want to: he was a journalist and author, after all.
Well, a modern distributism would almost certainly not work by giving everyone a little tract of land in the country. I think the point remains, though - if you give everyone a certain allotment of property, that property is going to change hands over time and you might eventually find it concentrated again. This is likely to just be a result of people having very different priorities in life. How does the distributist system cope with this? Do you ban people from selling or trading their distribution? Do you have some sort of periodic
Jubilee where you re-distribute everything?
Anyway, to come back to your suggestion - what would you do in the case of people with very different ideas about what it means to live well? Would this cause any issues for you?