Other than the need to maintain rail + power lines, I think these issues are overblown. The badly parked car scenario sounds pretty horrendous in theory - one careless actor causes chaos for an entire city center! In my experience it simply doesn't happen - I think people just know how damaging it could be (and possibly how much trouble they would be in) that they pretty much have to be considerate and self-aware.
However I have seen trams broken down temporarily (a couple of times in the last 7 years of taking 2 trips daily) but these get resolved surprisingly quickly with minimal fuss. Additionally I've only seen a Trolley lose its connection a couple of times, and the resolution took about 1 minute.
This is of course heavily based on personal experience, if you have experience to the contrary I'd be curious where this is. A friend complained a bit about Trolleys in Wellington needing frequently reconnected, but I don't know how common that is or whether they just had some bad luck