I think all of the property management companies offered to you in the previous emails are good suggestions. I've referred most of them at one time or another. The one I found did the best job was Stringer Management. I think they are probably the biggest in town. My clients have all said they did an excellent job.
Renting annually vs. seasonally is always a tricky question. It depends on your exact unit and their rental rules. If they are flexible and allow you to rent more often for shorter periods then renting seasonally may be attractive. It also depends on the location.
An annual rental is a sure thing as we have several clients who own condos that rent them out on an annual basis. Within 1-2 days of advertising their unit they have many qualified applicants and rent it right away.
Hope this helps! Let me know if I can do anything else.
Ron and Susan Noce, Realtors
Key Realty, St. Armands