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What is the main difference between UserServiceWrapper and UserLocalServiceWrapper? 

UserServieWrapper is class which Wrap the UserService  and UserLocalServiceWrapper is class which wraps the UserLocalService.  so if you  want to   wrap   localservice then you  use localServiceWrapper and for remote or webservice you use servicewrapper . You can refer below url also 
https://portal.liferay.dev/docs/7-0/tutorials/-/knowledge_base/t/customizing-liferay-services-service-wrappers
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Why is one working and the other not?

May be its not deployed correctly .You can try deleting your wrapper module and deploy once more 

What is the main difference between UserServiceWrapper and UserLocalServiceWrapper? 

To add a little more to what Mohammed added, the UserService (no local) is normally the entry point for an external call in. So for example, the JSON Web services. The normal development flow then in the XXXServiceImpl classes is to check the user and their permissions and if they are "allowed" you then invoke the XXXLocalService methods. If you are working with a component in your application (as in not coming in from outside) then you normally use the XXXLocalService set of services because your initial "Access" vetting has already been provided (because your user has logged into the portal already).
So in short XXXService normally provides additional or tighter security measures than XXXLocalService. Everything else, Mohammed answered already.

Ok, I understood the differences between the Local and Not Local, but I can't seem to make it work yet. There are two methods "addUser" on the UserLocalServiceWrapper class, I have Overrided them both to print a System.out.println("something") before the super.addUser(). Then I go to my instance control panel and add a new user, just like I did with the UserServiceWrapper, but this time my Overrided methods are never called. If i go to the Gogo shell and type "lb" I can see my module active, so I presume that it is correctly deployed.

How strange... I did a breakpoint at the super.addUserWithWorkflow on the UserLocalServiceWrapper class and it did pause there after adding an User. However Overriding this same method on my UserLocalServiceWrapperOverride class, this method was ignored. Also I noticed that when I start the server I get this Log:

2019-08-20 15:34:43.242 INFO  [main][SystemCheckOSGiCommands:111] Running "Declarative Service Unsatisfied Component Checker". You can run this by itself with command "ds:unsatisfied" in gogo shell.
2019-08-20 15:34:51.948 WARN  [main][SystemCheckOSGiCommands:134] Declarative Service Unsatisfied Component Checker check result: _Bundle {id: 1075, name: pt.globaleda.portalgra, version: 1.0.0}_    Declarative Service {id: 6, name: pt.globaleda.portalgra.wrappers.UserWrapper, unsatisfied references: _        {name: serviceSetter, target: null}

How silly I am... This was not working because I was setting my service wrong. On my serviceSetter method I was passing a UserLocalServiceWrapper instead of an UserLocalService. Don't know how this happened (probably a wrong copy/paste) but this was the problem. After solving this the service works as expected! Thank you both for the help!

PS: Next time I should paste here my entire class... Maybe you are not as sleepy as I am