I think "babysitting" only really applies to things that "just happen" at some random time, rather than things you basically explicitly signed up for doing.
Definitely. Colonies requiring extra stuff is fine, just so long as it isn't overly random. Or only able to be supplied once the colony actually demands something. Imagine putting down a colony, getting halfway to further exploration and suddenly the colony goes "actually, we need...eh, let me get out a d4 here...5d100 Food to continue working!", whereas the next colony demands 4d100 Domestic Goods, the next some amount of Luxury Goods and the next
Lobster (for some inexplicable reason) or what have you. That'd be...less than ideal.
You could probably integrate this into the colonization screen pretty easily, I'd say, the one that says you need 1000 dudes, 100 Heavy Machinery and 200 Supplies to found a colony. Have another box below that lists what
specific things that particular planet will need for a colony to reach the point where it'll be self-sufficient depending on the planet's conditions - say that every colony needs some amount of food/goods to tide them over until they can establish their own food sources, but planets with Destabilized Subpopulation specifically requires some amount of Marines to keep the initial colonists safe, tectonically active planets need additional supplies/heavy machinery to reinforce structures and build warning systems, High Gravity planets can require Heavy Armaments ("Humans require powered exoskeletons for regular movement and find even basic actions exhausting", which could be a part of the Heavy Armaments item, like power armor style?), etc.
The only real detail to remember (that I can come up with off the top of my head) is how to make sure that secondary list of required items is accessible remotely, without being at the specific planet. If the amount of items you need per hazard condition is static you could just look it up on a wiki and calculate it, or run around the core looking for planets with the right conditions and calculate what you need from that, but ideally it'd just be available from the Intel screen. That shouldn't be hard to add, though, I don't think.
Imagine if the endgame enemy was the Hegemony, and you were facing a couple of Lashers. Maybe with a pre-buff Enforcer thrown in there, to make it a challenge.
(It's possible I'm exaggerating a bit for dramatic effect...)
I'd just like to note that Frigates and Destroyers individually have killed me more often than Cruisers and Capitals combined. So in terms of fleets that have an actual record of making Swiss cheese of my hull
...