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Buying an upgrade several times takes the money but doesn't increase anything. Probably as it should be, but maybe explain it somewhere or change the upgrade colour.

(+1)

It is explained in the game description:

That means you will only ever be able to have one upgrade active at a time.

And besides, I did the same thing and realised after buying it twice that having more than one did nothing, just as the game description explains.

The description was clear that you can have only one job, but it didn't say that you can't upgrade the job you have and you'll only waste money by buying it again. The active job should be grey and unclickable imho.

Understandable point of view, but it should only take a loss of $50 to realise that one job means one job. Maybe $100 ;)