Yes, it will catch up.
IMO,
5 years of time, the HDD or USB stick could be corrupted in hardware level. Low probability but could happen.
Preparing 2~3 USB sticks and storing identical wallet.dat file will be safer to keep it long. Also, check both USB's condition once a month, by mounting onto "linux or mac, offline computer" I wouldn't consider windows as a safe computer.
Lastly, if you encrypted wallet file, 5 years could be long enough time to forget your own password. There's no such thing as "reset password". Be very careful not to forget.
I appreciate the response. This pretty much answers my question. Yes, of course multiple immediate copies on multiple external storage. Perhaps even burning a copy of wallet.dat, a copy in .rar and .zip of the same file over multiple dvd copies would achieve the same purpose.
What about code changes or even "forking" as I have seen with some Alt-Coins. Does that not require some changes to the wallet.dat to remain valid?
DVD-R or CD-R would be a good idea because they are cheap and guaranteed read-only.
I strongly believe bitcoin-qt source code contributors would do their best not to compromise old version wallet...
With many years, attackers may find a security hole, then dev team may have to compromise old version wallet file format. This case will be a very big news and dev team would announce proper wallet upgrade guide... I can't imagine more details for now...
If any attacker can hack bitcoin(or blockchain) by completely dominating dev team, so quickly that lots of wallets could be already stolen, that will be the end of bitcoin. Even alt-coins will lose trust that case. That could boost physical precious metal.