Everyone else commented on the danger of non-black start issues. If you've got live grid to connect to and sync to, why would you ever black start anyway? Or more precisely that has nothing to do with the "fun" of black starting.

The actual EE-ish problem with black starts is that darn control systems class the EEs have to sit thru full of bode stability plots and stuff.

The problem is that power plants and the innards are kind of like highly tuned race car engines. The peak of technological performance at 1000 horsepower out, but at idle they get kinda squirrelly and don't really know what to do so as not to oscillate and/or stall and/or blow themselves up. For the signal/telecom EE types, black start is kind of like having a very high power finicky high gain amplifier with no decent termination and no real input and not much control, the odds of that dude deciding to oscillate are unfortunately high. Another way to put it is "the grid" is more or less predictable constant impedance you can smoothly and predictably match to, but connected to nothing during a black start or initial power up is very much like keying a high power radio transmitter when not connected to an antenna or dummy load, its going to be pretty impressive no matter if it blows up or not.

Theres some interesting impedance issues. An alternator is kinda like a constant current source, for a given field winding current it'll squirt out a much higher current from the main windings. And inductors don't like to change their current flow. And the only limit to the voltage is arc over and/or the internal resistance of the winding (well.. AC is much more complicated, but..) So overexcite the field winding on a connected gen and the voltage across town goes up a hundredth of a volt who cares. Overexcite a unconnected / black start gen and it could just arc over and explode or blow transformers and just F the place all up in general. Dump an extra megawatt-hour of energy in the general direction of Chicago and Chicago doesn't sniffle, dump it into one little piece of switchgear in the yard all by itself because its disconnected / blackstarting and the arc blows it to pieces.

Another issue not at his relatively boring gas turbine plant is stuff like differential thermal expansion. You have to heat and cool boilers and steam turbos slowly or else differential expansion can rip them apart. Supposedly if you leak even a little steam on a stationary turbine it'll expand one side enough while leaving the other side unexpanded and cold that when you slam the valve open its an open guess if you'll destroy the bearings from vibration or smash the blades into the outside of the turbine. So you keep them spinning, even if its really slow like 10 RPM, all the time, forever, unless you've got a crane on site to replace. And boilers blow up if you heat them too quickly, same problem with parts at different temps.

Gas turbos are tougher than steam turbos for a variety of reasons one being they're so dang hot and so much outside air (full of bugs and stuff) flows thru them that they can't build to the tolerances that a steam turbo can use, so they don't even try, so powering one up isn't as exciting as you'd think. Oh its loud, but not as exciting as spinning up a steamie.

Another fun feature is black starting is pretty hard on your whole backup system. Idling the diesel for 15 minutes a week is not quite as exciting as slamming it open full throttle for 12 hours while you heat up the main boiler or whatever. So if you're going to blow up your UPS / diesel / whatever its going to happen at black start time.

There's a general engineering rule that its a heck of a lot easier to design something that constantly does the same thing than something that varies, maybe randomly.