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When you say "Skip some tools" you mean that you have a select tool before the Join that shows they're the correct type before the Join? If this is the case, it's not skipping the tool, but that Select tool isn't forcing the field types like you think.
To ensure the field types of your join fields are the types you expect, there's a few things I'll recommend:
1. In the Select tool. If it auto-configures [Currency] to a V_WString, then you should be able to go into that Select tool and a new option will appear as "V_WString: Forced". Right now it's just displaying the types that were fed into it when you built it in designer, this new option appears after it's been run to force that type.
2. That option is pretty weak as far as forcing a field type goes. The better way is the Multi-Field Formula tool. This tool is extremely powerful not only because you can operate on multiply fields, but also because you can FORCE the type in the same tool. Configure the tool something like this to force string field type type of the same name and "value" as the current field. You'll need to use a second Multi-Field formula tool to force numeric types:
3. Finally, this issue is ultimately coming up because the inputs changed types from what the workflow was built for. I'd also recommend avoiding this from the start by using Test tools to throw an error if the inputs are not the correct field types for the workflow. Stop it before it starts with the added bonus that you can write your own custom error message that let's the user know what to do like "The Currency field is not a string. Update the input file and try again".
So what's happening here is that your are getting a type mismatch. When you upload a file into Alteryx, it automatically identifies the field type to the best of its ability. So if you have one file being uploaded where currency is recognized as a double, and then another where its recognized as a string, then these two fields cannot be joined together.
The good news is that you can build your workflows, macros, and apps to hardcode the field type you want. It just takes a small little Select tool workaround.
Step 1: Connect a Select Tool to your incoming data, and set the desired field type.
Step 2: Connect a second Select tool to the first one, and use the drop down to select that field type as "Forced".
Step 3: Right click on the first Select tool and choose the option Delete and Connect Around.
Now your incoming data fields will be forced to their desired field types.
The reason you have to connect two Select tools is because after Alteryx identifies the field type from the incoming data, it will only allow you to set that field type to "Forced" for the type it recognized.
If this solves the problem please mark answer as correct, if not let me know!