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I feel like around 20 months to 2 years was another turning point- which of course is why I ended up getting pregnant with my second! It's definitely ebbed and flowed since then though.
But I remember before 18 months I couldn't fathom how anyone ever had a second kid on purpose, and at 20 months I thought, ok well maybe we could do this again...

Now my second kid is 21 months and I can't fathom how anyone has three kids

I was also going to say 18 months to 2 years old. Consistent eating and sleeping, developing interests in toys and play with us as well as more imagination. It's continued getting better now at almost 3. Around 18-24 months he also started showing interest in educational apps and tv shows so in a pinch that would give us a breather.

Around age 2 when she finally started sleeping through the night. At that point I felt I could definitely handle another. It had been a gradual process though, definitely started getting easier prob around 18 months on? It was a combo of her getting easier and me being more used to being a parent with all the responsibility it entails!

I agree with 15-18 months. I know a lot of people start TTC again in that period because you finally catch your breath a bit. This morning DS (turned 2 in june) cried and needed to be held from the moment he got up until we left the house for daycare. All I could think was "How did I live like that for so long?" He's still not a piece of cake up it reminded me how far we've come.

DS1 was a lot easier at 2. He could express more even though he was speech delayed, he was feeding himself, he could sit and watch a show if I needed him to, and he understood disciplining like timeouts. He knew not to hit his baby brother (our kids are 20 months apart) so that was also great.

With two kids, we started hitting a good groove where I wasn't constantly worried that DS1 was going to accidentally kill the baby by smothering him when DS2 turned 9 months.

They are 36 and 16 months now and they get along wonderfully.

I think it depends on the kids as well. my almost 5 year old sometimes requires more attention than my 19 month old (and it has been like this for a while). He only started being okay to play by himself in the past year i think. whereas my younger one is content most of the time to sit by himself and i can get a ton done....it;s only harder now that he is in full on toddler mode and likes to make messes everywhere and every minute!

It really depends on your kid. My oldest is much more clingy and required much more of our attention. My youngest is very independent and was happy to play by himself from a very young age!

They are now 2 and 4 and play together or alone very well. I would say by 2, my oldest (clingy one) was willing to play independently for short periods of time. Now at 4, he spends his "nap time" playing by himself for two hours straight.

I feel like this question is completely dependent on the personality of your kid. High needs baby always wanting to be held, not sleeping, etc? That's probably miserable. Cranky annoying needy whiny tantrumy toddler? Probably no fun. My kid is great at independent play, from a very young age. I wouldn't say the baby months were awful...but the sleep deprivation was miserable.
I feel like it's an ebb and flow. There is a always a challenge, but milestones like crawling walking and talking make things easier and harder to some degree.
We are adding #2 in December and I'm just anticipating everything to be more difficult, in general.

Easier? What's that?

It gets different. As kids get older, the problems become more complex and involve other kids that you can't just solve on your own with an adjustment to a schedule.

After we sleep trained at 4 months. We were sooo exhausted it was life changing once Charlie was sleeping well. The next point that it became easier was 15 months. Talking, walking, much more independent, and so much fun!

As much as I thought the infant stage was hard though, the 3's+ challenged me much more. It really depends on the child, you and so much more. It's easier in some ways and harder in others with every stage.

My LO is 13 months and I feel like she's a breeze at home. She can actually entertain herself. The floors of my house are pretty well contained with baby gates so she can wander around while I'm in the kitchen doing stuff.

I think going anywhere outside of the house is very tough at the moment. She wants to walk every where, and wants to usually go in the opposite direction we need to be going. And then she pretty much never wants to leave the place we are at. She's so opinionated already. It blows my mind.

@Eminthevalley: You DEFINITELY do I’m always in awe of multiples moms!

I'd say around 20 to 24 months, depending on the child. (I'm on #4)

@looch: Agreed!

In the first year, LO1 was super colicky. So it got easier after about 4 months when we were able to sleep train him and he started coming out of his colicky stage. Once he turned a year, it got hard again. From there, it ebbed and flowed in easy vs. hard. Right before language bursts was always really tough with whining and not being able to express himself very well. He's 5 now, and he's delightful, but does go through being bullied at school. He seems to be a target because he's super sensitive. He reacts to everything which just feeds the bully, and it's really hard to watch without being able to do much.

LO2 was completely different. He was a dream baby through about a year. Once he started walking, he turned into a very energetic runner and always wanted to be down and in things he shouldn't have been. He's now 2 and getting better, but he's starting to be purposefully defiant to test his boundaries. So this is a hard phase with him. He's far more vocal than his brother was at this age, so he's not whining as much...just being super defiant and spending a lot of time in time out.

Honestly it depends on the kid. There's no magic age. Right now DD at 2.5 self entertains less that she did a year ago.