In short, either things end poorly or things end well.
Lopahin and Ranevsky follow different dramatic trajectories. Lopahin's is comedic. He may not get married or start a family, but he begins the play as a successful merchant and ends as a property owner, with a sizable estate his ancestors had been legally tied to as serfs, and he can use to increase his wealth.
Ranevsky's is tragic. She begins the play returning from France where she has squandered her wealth on a lover. She's in debt, but either refuses or is unable to acknowledge it. She longs to see her ancestral home and pines for tradition and is glad to have her home. She ends, however, ousted from her ancestral home to pay her debts. Her home, her heritage, her tradition, all lost.
And then there's the fact we're dealing with a play. Unlike poems and stories, plays are a public affair, with actors, a live audiences, and carefully designed sets and stages. A play is a communal experience in a large room filled with people. Even film was like this until the advent of television, VHS, and home entertainment.
People who have time and money attend the theater. Even today if you're going to see a professional play, you're going to spend upwards of a hundred dollars. Compare this to a feudal society where being a serf (like Lopahin's ancestors) belonged to the land and no land belonged to them. The lower classes never had the means to go see a play. It wouldn't be until serfdom was illegal and social mobility possible that someone other than the upper class, like the landowning gentry Ranevsky, could go attend the theater. While I can't confirm it, I like to think the audience of this pre-revolutionary play were mixed. Some traditional gentry on their way out, and some up and coming middle class. Those who had lived their lives with the theater and others whose parents had never had the chance to sit and watch actors and actresses play their parts.
Which characters, then, would this diverse audience have sympathized with? The distinction is hopefully an easy one to make:
The rising middle class would have sympathized with Lopahin, feeling for his rise from poverty, ingenuity, and his success in securing an estate. For them, the play is a comedy as they would have empathized with his personal struggles and successes, seeing a version of themselves and their own aspirations embodied in him.
The old aristocracy would have sympathized with Ranvesky. They would have seen the noblesse oblige embodied by Ranevsky in her parties and charities, and feeling for her as they see her succumb to the loss of her estate, which they would have all considered a tragic loss.
Whether or not Chekov intended it, and whether or not directors structure it accordingly, The Cherry Orchard can be a divisive play as it sends its characters in different trajectories. The play shows the delicate balance between comedy and tragedy with the play looking one way and then another as Ranevsky and Lopahin engage with one another, their situations, and the rest of the cast. It has the potential to remind us that happy endings are not so clean cut as we like them to be, and that our happy ending may be someone's sad ending.
But there’s another side to this issue. The play and its themes are deeply rooted in a different time and place from modern audiences. As a teacher, it is interesting not just to discuss where the sympathies of contemporaries would have been, but also to deconstruct our own reactions to this play charged with social commentary.