Go to the library and find American Theatre Magazine. Once a year they publish a list of the announced seasons for as many of the LORT theatres they can get--hundreds of theatres. The issue usually come out in late summer or fall.
Go into the stacks and get the issue and sit down and skim the seasons.
What is your budget? For the season and for each show? Most theatres do small cast shows that often have less than elaborate sets and can often be played on a scaled down set plan.
If you do five shows, think a well-known commercial play, a well known drama, a classic, a not so well known work and a small musical. There is a reason Proof was widely performed its first year that it was available: it was good, it won the Tony and the Pulitzer which could be used to plug the show and it had one set where nothing flew and used only 4 actors. It was cheap to put on.
Think along the lines of The Star Spangled Girl (Neil Simon, 3 actors, one set), the aforementioned Proof, Dear Liar (2 actors), and I Do! I Do! (2 actors). The last has been done and done and done to death, but there are only two characters.
You don't have to do these specific shows, but they are all cheap to put on.
As for the classic, nothing pops into my head except large cast comedies like She Stoops To Conquer from the 1700s. However this is a crowd pleaser. Many roles (maybe 16-20), many settings but they could be suggested with props only, and period costumes some of which might have to be built and some could be pulled from stock if you or any other companies have a costume stock room.
Never rule out a terrific and very funny and clever play called Greater Tuna: two actors, about 20 roles, simple sets and not complicated costumes. You do need a large running crew: each actor needs their own dresser, plus lights, props and sound. Find the dvd with the original actors/writers. You'll see what I mean.
Publicize by taking ads almost anywhere, use direct mail, write stories for the local papers even the throwaways, posters where people congregate, school group discounts, senior discounts.
Any play that is really any good will work with virtually no sets, a few essential props, rudimentary lighting and suggested costumes. Every play that you read or see, take away the physical production in your mind's eye, and if the play still works, then it is worth considering.
"If my life weren't funny, it would just be true. And that would be unacceptable."
--Carrie Fisher