Mahoromatic: Automatic Maiden

Both anime are about women with strange powers who decided to became maids. There is some resemblance in tone and style that makes me think that Mahoromantic influenced Kobayashi-san. 

Both have a cute, over-powered non-human maid who is deeply devoted and in love with their master. They are also both slice of life with some drama sprinkled in. Both deal with the theme of running out of time to spend with your loved ones. Most importantly, both have ecchi humor ;) I prefer Kobayashi's Dragon Maid, but they both have very sweet moments. 

Two powerful maids and a roommate of theirs slowly form a strange relationship between each other, accompanied with goofy but charming characters. Along with weird shenanigans there are also serious moments along the way, mostly around the worlds where the maids come from! Both shows are colorful and have stunning animation, very eye candy! 

They both show a boy living with a non-human girl. They also have a perverted female teacher who likes to get in the way. 

The perverted, intrusive female teacher , the maid/servant and overall mood is very similar. One has a aliens, the other has a robot, but both are unfamiliar with normal humans and idealize their master. The two shows belong to the sudden girlfriend genre, only with slight differences.  

Both Kimi wa Meido-sama and Mahoromatic feature a male protagonist living an ordinary life until it’s turned upside down by the arrival of a maid seeking employment. Despite her reserved emotions and shadowed past, the maid brings a unique charm to his life. Together, they embark on a journey to uncover the hidden beauty in everyday moments, blending light-hearted humor with subtle, heartfelt connections. 

The story goes with a girl conflicted with her past going to serve in the house of a young boy. In some point they fall in love with each other and so on. In one side we have an assasin (Kimi wa Meido sama) and on the other side we have a kinda loly combat robot (Mahoromatic) 

Mahoromatic's love story is a tad bit different than Chobits, but in general, there are many similarities between the two shows. It's worth noting that one of the driving elements of this series is that Mahoro, the main female character, is actually going to die...in 390 days from the first day you're introduced to her. There's actually a countdown showing how much time she has left at the end of every episode, and it's a very powerful tool in intensifying your desire to see the main characters realize their feelings for each other. There are some very obvious differences between Chobits and Mahoromatic, and they're apparent just by looking at the cover art. Mahoro is not in the same class as Chii in the least. First off, she's a bit more attractive (opinion of course) as she is designed to look like a 19 year old girl as opposed to Chii who looks 13. Mahoro is also nowhere near as innocent as Chii; she's got plenty of real life experience, and has seen, and taken part in the horrors of war as the worlds most powerful combat android. That said, being she has very limited time left to live, she's given the opportunity to live life as a normal person, during which time she decides to become a maid. Carrying over her unwavering loyalty to duty from her career as a combat android into her new job as a maid, she still manages to run into predicaments similar to those you see in Chobits, albeit without the same level of innocence and lack of common sense as Chii. Suguru, the male lead in this series, is actually quite similar to Hideki in his awkwardness and appreciation for his companion. If you liked Hideki, I can promise you'll find a lot to like in Suguru...though he does have a bit more smarts and common sense than the former. The only thing I found odd was adoration the opposite sex has for him throughout the series. It seems that almost every female in the show has their eye on him, while he isn't really portrayed as anything more than your average guy in any regard. I should mention that there's something of a difference between the first season of this show and the second. While it's not as drastic as, say, Gunslinger Girl, it is there. Animation and art is left largely intact, though the second season is far more vibrant and colorful; it overall looks better to me. The story is left largely the same, however the focus shifts from romance with comedy to comedy with romance. It still balances the two well, and maintains its charm, but there is a transition period. Still, once you get used to it, there are some truly laugh-out-loud funny parts, and one episode where I actually had to pause it I was laughing so hard. In the end, I think you'll find the show to be just as charming and entertaining as Chobits, and Mahoro to be just as endearing as Chii. read more 

Both involve a robot female love interest for the protagonist who also work for them. 

Gainax pretty much made both of these shows identical in the style/tone/comedy and just the overall feel. Hell, they even look like they used the same models. It's not much of a stretch to say that you'd like both. 

Indian Summer (Koharu Biyori) also explores the concept of a maid robot, but with more emphasis on pervertedness and nudity. Where Mahoro is sweet and kind, the main female in Indian Summer is sweet and angry. Indian Summer is a short series of 3 episodes, with random funny bits thrown in (the baby episode was my favorite) but is more aimed towards ecchi fans. 

Both series have a lot in common in a general sense. A young guy gets young maid/s to work for him. Both series were done by Gainax. Also both have a similar sense of humor. While it takes the similar concept as He is My Master, Mahoromatic does ever thing better. Mahoromatic has a far better story, is funnier, and ecchier.