@Alexa M. Welcome to BP. I would certainly at the very least get a property manager, the idea of using a resident manager is also one that has had success but I would make sure you really trust, think of them essentially as a partner in your business seen as their choices and decisions directly impact your business and investment (pick someone that is responsible) another part of your team I think would be vital to your success is a handyman that you trust, someone that can handle small repairs quickly and be trustworthy and knowledgeable enough to know when the task is outside their ability and can let you know, the manager know to contact an actual specialized contractor or if you trust them enough allow them to arrange and coordinate the hiring of contractors.
Obviously I would definitely consult with an attorney and get a contract drafted up for each of the people on your team so there is no questions as to who is responsible for what. It alleviates most confusion when it is in writing, and protects all parties. Though you may not need that with a handyman I would still bounce the idea around with legal counsel. But most definitely if you use a live in manager map out exactly what you expect from them and what they can expect from you in return.
Hope that helps you, any more detailed questions feel free to ask or PM.