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The only problem your request has is getting the data into the game automatically, as Fizzle explained this isn't possible. But it doesn't stop you from manually adding items into an addon that creates a list ( table ) that it uses to do what you want it to do.
Suggested Avenue:
a) Outside of game your python script is doing its stuff and lets you know what you need to know
b) You then manually put that information into the addon that has a section that handles storing of information for using later.
c) Another routine in the same addon, then uses that information to handle the auction house tasks
As to your numerated queries
1) You may be able to target someone nearby by name using /target in a macro, otherwise, you may have to target them manually.
2) Your addon can have a button on it that using a keybinding can call a function that starts the search functionality you want and addons are allowed to do.
3) How lightweight it will be I don't know but whether you are scanning for one or more item types you will likely be scanning the auction house to get the information you need.
How you would go about this in more detail I can't help you with as I only briefly looked at the auction house system as I don't need to customize how that part of the game works.
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