From the AWS buddy point of view:
- I'd say don't try to fly too far with small A/C. A general rule is not flying further than 10 x total seats of your A/C. Well, this is what I heard from other people who have experience with small A/C
- You're still small, so better focus on closer airports, so you can get at least 4 flights a day per A/C. Flying to ORD would be your last option after filling all other routes
- And to answer you question, use a no-bigger-A/C than your competitors, and serve the route 1 or 2 times daily. You'd be able to draw decent (better) LF when all other factors are equal (RI, CI, proper A/C, price, time, etc...)
From the competitor's perspective, I'd welcome you to join the route. The more, the merrier, right?