What are my legal options to collect a $2,700 debt?

You can go to small claims court or hire an attorney. Even if you get a judgment against him, can he pay it.?

Your only recourse will be to sue this individual. Note that if you him, you could also sue for additional direct costs (not legal or court fees, however) incurred owing to his bouncing checks--such as any bad or bounced check fees you incurred. Depending on circumstances, you might also be able to get interest (for example, if you have a notice on your invoices or sales agreements that unpaid invoices are subject to interest). Be aware that if the customer has no money--e.g. it's a business that's gone out of business--there may be nothing you can collect, regardless of whether or not you win in court.