Most importantly make certain that in switching to QBO you don’t loose any functionality that you are used to in the Desktop versions. 
QBO is a great platform, but it doesn’t handle special adjustments or situations well. Such as special use of items, or non standard tax calculations. Particularly if you are growing and could exceed the 14,500(?) item limit, and could find a jump to the Enterprise version a possibility. In which case you are better off setting up a hosted version either on your own or other server.