I think getting your current system running smoothly may be simpler than going to the cloud. Probably the biggest difference in the cloud is decrease in tech support, but you have a good IT person. It might've something to consider, but get your other problems solved first.
Since the data entry issue is not a significantly time you have some time to get your future billing options together. If it ain't broke.... Yes, you will need something better in the future, but take one step at a time.
Hopefully your current space problems will be solved by paring back old backups. If this is the case, you can then focus on the other 59 hous in the work week. You will need to address these issues in the not too distant future, but can parcel out time to get it done
