I was like you and did everything. Of course it was always just as I preferred. After a bit of growth, that was impossible so I hired a US based VA and an overseas VA and life is so much better. Plus I can now focus on company growth and strategy and not the mundane.
What really helped was an operations manuals. It has taken over a year to write and I tweak it every day. Every task that I did was documented in the manual. I even recorded audios and videos on topics varying from “preparing leases” to the most mundane like “document scanning and filing.” The first 5 pages of the manual include a task schedule for 1) daily tasks (e.g. check voice mail), 2) weekly task (e.g. check PO Box), 3) monthly tasks (e.g. mail statements), 4) quarterly tasks (e.g. prepare income statements), and 5) annual tasks (e.g. send rent increase notices). Every task is scheduled to a specific time. Now, when somebody asks me how to do something I say to look at the manual and if they don’t understand, we tweak it until they do. See partial image of schedules.
The overseas VA does everything from taking phone calls for the whole company, bookkeeping, taking applications, taking customer service requests, emailing prospects from Craigslist, Zillow, etc., scheduling showings for park managers, and handling level 1 sales inquiries (simple things like explaining home inventory and rent amount). If I could say there are a few big things that were best to outsource I would guess they are 1) phone answering, 2) bookkeeping, 3) tenant customer service, and 4) accounts payable.
The US VA is also a park manager and she schedules maintenance across all parks, handles level 2 sales (more complex questions), and prepares leases.
To organize all of this, we have a NAS server that is web-enabled with file folders and various permission for various users. Almost every document we receive is scanned to a virtual inbox on the NAS and the VA organizes and processes the files as needed.
You will find that tasks take longer, don’t always get done the way you would do them, etc, but in my opinion, that is a cost to doing business and necessary if you want to scale.