I'm currently playing an 18th level fighter/paladin in a converted Age of Worms campaign. Maybe it's just because the DM's been converting stuff over from 3.5, but for the last few levels, the game's felt a bit too easy. We can deal a lot of damage and take a lot of damage, and we can do things that bypass a lot of stuff that would've been challenging a few levels earlier.
I agree that solo monsters are too easily dispatched. The last big solo boss fight we had was with this monstrously huge carrion crawler. The DM had given it legendary and lair actions, but those hardly slowed us down. We dispatched that thing with ease. I want to say that giving it minions would've helped, but it would've depended on the kind of minions.
An earlier fight we had consisted of a horde of undead creatures trying to scale a slope while some monstrous skeletal dragon thingy loomed over them. My paladin used plant growth to slow the horde's advance and the druid shapechanged into a gold dragon and that was that. We picked off the horde easily from a safe distance, while the druid dragon dealt with the skeleton thing.
I'm glad to hear that other DMs are still able to challenge their high level PCs, though. It's possible my DM just hasn't figured out how to do it properly yet.
It's a hell of a lot of work converting stuff at high level. I've spent 8 months converting 41 pages of NPCs and creatures from City of the Spider Queen - usually spending a few hours a week. But the results have been satisfactory.
Your DM may be just reskin things which IMO will result in a subpar challenge.
Also 3rd edition stuff generally seems to have lesser numbers of creatures, and sometimes assumes an encounter that is 1-2 levels higher is a 'tough fight'.
A solo creature in 5e needs to be at least Level + 5 generally to be a deadly encounter, and lots of encounters with only a couple of creatures will be too easy for a high level 5e group.
What I do is look at the module and go "Ok, it wants a EL18 encounter". I'll then keep the spirit of the encounter intact, but I'll make creatures that will equal a "Hard" encounter for a level 18 group (I do "hard" because of the magic items my group has). If it's obviously meant to be a rough fight, I'll make it deadly.
If it's a powerful NPC I will usually give them a couple of low CR minions (usually CR5 for this level). 3e assumes casters and such are running around with a huge number of buffs on, instead 5e you need minions instead of buffs.
At your level your average encounter against a solo should have 300+ hit points and a decent AC, along with the ability to do about 120 damage per round. Does it feel like that?
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