In reality, decent quality regulators should cope with some flooding. This is why the regs should be serviced as some parts may corrode such as the filters. However, if it’s used and not left wet, it’s probably not going to be adversely affected.
Note the use of probably, should, etc. There’s a risk and it’s your decision.
So, what’s the main benefit from sidemount…? Redundancy, ease of switching, etc.
In multiple gas diving — aka accelerated decompression— it’s normal to power up the regulators to check it then close the valve before jumping in (you don’t want to breathe the oxygen rich gas at depth as it’ll kill you). Inevitably the regs will leak if knocked/purged or if the second stage dribbles/free flows. One periodically checks but it’s quite common for the reg to flood. It doesn’t seem to create long term problems, certainly in my experience anyway.