Clean Up/Reorganize My Customers & Jobs List

"Going through the list is getting more difficult with the growing number of jobs added each month."

Make old job names, and even Customer names, inactive. Example: I have only X I am working with routinely. The others, I Activate them when I work with them, then make them Inactive after the payment comes in, and I won't hear from them for 9 more months.

"I have a couple customers that have multiple locations and are billed monthly, one prefers to be billed twice a month.  With that customer alone if I do work at all seven locations during both billing periods that adds 14 new jobs each month under that customer alone."

"Adds" new Jobs? You alreadu Have the job, though. If you are creating a new job for each Work Scope, that would be the error. Working at the same loation over and over = keep using that Same Job and keep invoicing that Same Job for the New Charges. You might have, for instance, Monthly charges for years and years, all for that One Job Name = how often you worked at the one location. Think of lawn mowing and snow removal services. That is Monthly invoices, but just the One Job name = that one location, over all those years.

"I get error messages concerning reparenting and the software will not let me perform the suggestion."

I think you are asking about Merging all those names. Example:

I manage property and you are my Yard Crew. You set up my name as Customer and each of my property is a Job. Now, you realize you could have been Invoicing the Job level, but you keep adding a New Subjob for that month? You have "Smith:123 Easy St:January" and "Smith:123 Easy St:February" and "Smith:123 East St:March" and now you realize those should be Merged. All you should have is "Smith:123 Easy St" and all the charges and payments and acitivity is for this Customer:Job. Yes, you can Merge them.

"Is there a way to either archive jobs (after reading the horror stories on how bad QuickBooks Condense Data feature works I have been afraid to try it...) , or is there a way reorganize the hierarchy into multiple levels such as by year"

You don't need Names by Year, at all. The transactions already have the year on them and the reporting uses that. Why would you want Year as part of Name tracking? Example:

I have a client that does Training and uses Year as the Customer name, then Students as the Job name. That is because they do Certification and Professional Licensing training. But, if you go to more than one type of training, that is Items put onto Invoices, for your name and that year. Not Your Name again and again.

Then, Sales by Customer can be fitlered for that year (customer name) and the Training Items, to see who attended which clases for licensing, for upcoming expiration management.

"On customers I do service work for and bill on a monthly basis, I was taught to create a separate job for each customer each month"

That was never necessary and this is the issue. Think of a day care; the Child exists Once on the customer list. Not Monthly.

"I am open to any suggestions"

Whoever trained you had a starnge concept. When you go to the grocery store, you are the Same Person that was there last time. Not a New Shopper each time.

"and have no issue upgrading from 2014 if it will help solve my issue."

You should be updating, because QB 2014 reached end of life in May 2017. This won't change that you got some strange guidance. You can clean up that list and stop micro-managing it, any time.

You want to Merge these. Like this:

Customer:Location <== you charge this and track this and report this, because you did all the work here.

Or, Customer:Building:Unit <== such as, you clean carpets and work with Property Management Firms and they care about this level of detail.

Let's review how to merge Jan and Feb and March, etc, for the same Customer:Job.

Make a backup, in case this doesn't go well. There is no Unmerge, but you can Restore from before you tried something you don't like the end result of.

"I was taught to create a separate job for each customer each month and use the numbering system"

If you have a reality of Customer:Job, such as WalMart:East Store... but in QB you have WalMart:2017-101 and WalMart:2017-102:

Edit the Job name 2017-101 and Change it to East Store.

Edit the Job Name 2017-102 and Change it to East Store. You are told this name already exists, and asked if you would like to Merge Them? Yes, you would.

Keep editing and Renaming the Jobs, until what you have in QB matched Reality:

I work at different WalMart Locations.

I work at the East Store and the South Store. I invoice for those two locations.