In many jurisdictions much of the EULAs are unenforceable for this reason and others; they are effectively a set of false assertions about rights and prohibitions.

Most EULAs are basically meaningless in the USA. Once you have a legally acquired copy of the program the Copyright Act specifically and explicitly gives you the right to back it up and load it for execution. You don't need to be licensed a legal right you already have.

You can also print it off, cross out the shit you don't consent to, initial the changes, sign, and mail it certified to whatever their address of record is. I'm not a lawyer, but at that point my understanding is it's their job to say no we don't agree, just like it was your job to say no I don't agree.

California rental agreements are a particularly odious example. Liquidated damages (AKA late fees) are completely illegal in California. In fact it's illegal to even present a lease that has a LD clause to be signed! Sometimes I wish I were more into small claims swashbuckling, because I bet you could have a dozen small claims for various properties going against Equity Residential in any California city.

How often do EULA/TOS type documents actually get tested in court?

I had a prof in university who was pretty sure majority of them wouldn't stand up to an actual legal case.