Uploading Contact Changes w/ Possible Duplicates?

I'm wondering if anyone else had done this, and either what method is most successful, or what pitfalls you ran into. 

I want to start capturing information about our event history in Insightly. What I plan on doing is uploading a spreadsheet to the system, and having anyone who attended be tagged in Insightly as, for example, #MayEvent2020

The goal here being I can run a quick report to see how many people from which sectors (something already tracked in the system) attended which events. We're hoping to use this to better plan events, and create marketing materials for potential sponsors. 

I have a few questions about this I'm hoping the community might have advice on:

  1. It's highly likley that some of the list is already in the system, and half isn't. I won't know prior to the upload without significant manual labor. Is there a way to resolve this from creating duplicate entries?
  2. I'm hoping to reduce this by uploading this information to accounts using a Name/Company filter so that Bill Smith will get tagged, only if Bill Smith is listed as working for Company X. Is this something that's doable?
  3. Will the system modify existing accounts (based on the criteria in #2) and create new accounts with a single upload? Or will I have to create two uploads? 

Alternatively, if you have a better way of achieving the same result through different methods, I'm happy to change course. 






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