I think this depends on a lot of different things. I've migrated a few medium sized sites in less than that time.
Instead of doing an actual upgrade, I've gone with a "migration" instead. This means setting up a new solution, and then importing all the content and media from the old site to the new site. I've set up the content types and data types manually one the new site, but you can migrate these as well.
I've used my own
Limbo Migrations package this, but I think most in the community are going with **uSync Migrations**:
https://github.com/limbo-works/Limbo.Umbraco.Migrations
https://github.com/Jumoo/uSyncMigrations
If you stick with upgrading, you might still have to convert data from their old format to their new format. I think most of Umbraco's picker were using UDIs instead of IDs in Umbraco 8, so this shouldn't be an issue. But if you have any custom property editors, you'll likely have to convert the values of those. Also the grid and Nested Content has been deprecated, so if you've used those, you need to convert their values to Block List or Block Grid.