For me, the hardest part is knowing when to stop.
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That's actually an easy one... ugh... never?
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See...this is where I get stuck.
That would work...96% of the time. But, that would also get triggered if we're gaming and someone walks through the bedroom to use the bathroom. Now...I gotta solve for that 4% before I do anything.
I think this is where the new batch of occupancy sensors coming on the market will really make a difference - like the Aqara FP1 - you'd probably still need motion sensors for fast response though.
Start with the button and once you get everything working, all that's left is replacing the button. I think it's harder than it seems to get the non-button part right. It's easy to think "when we're in bed..." but what about the once a year cases? Both are sick and in bed...
Once you get it all working perfectly so that 'replace-the-button' is the last remaining step... there may be tech that helps. 
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"What do you find hard about home automation?"
Leaving it alone. I'm constantly trying things out, looking for something else to automate, creating some newfangled complicated rule. I'm messing around with some part of it nearly every single day. It drives my wife nuts!
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Yep, those corner cases are a PITA 
Blue Iris is a Windows program. I run Linux. BI is a non-starter for me.
I do "no motion in living areas for 45 minutes after 10pm" before a switch to Night mode (which really just turns off lights and locks doors if they aren't already). It simulates the old Smartthings "when things settle down" function. After it's in Night mode, it won't switch to Home until motion after 5am, so even a midnight snack doesn't change it back. It works really well if we go to bed at the same time or if one stays up later or we have company.
As for what I find hard... My brain doesn't connect with Rule Machine at all. Thankfully, webCoRE also works on Hubitat. I'm not a programmer, so thinking in rule/piston syntax and logic took a bit to get used to, but my 50+ pistons are humming alone happily.
As a side note, I originally started with Stringify on Smartthings. I loved how it was visual, but I moved to webCoRE when Stringify went away. It looks like NodeRed is very similar with visual flows, so it intrigues me, but again, I'm not a programmer and the thought of setting up anything more than a Linux live boot CD is more than I want to get into.
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What do I find hard about home automation?
Knowing when to stop.
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I know that feeling. Just added 6 switchbot curtain bots and dont feel like putting them up. But I just had to have them because they were 50% off.
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I keep an inventory of parts - lutron switches, Hue lights, contact sensors, water sensors, motion sensors, even a spare hub - in the basement so I can be spontaneous in my automations. And I sometimes see something, buy it, and stick it on the shelf knowing "someday" I will need it.
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Yep - definitely do the same.
Sadly just bought some of those FP1 sensors I mentioned..
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My wife.
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100%
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I've found if you reboot them occasionally, they are much more responsive.
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And by reboot, I mean give them lots of love and attention. 
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I'm coming from an educational background in computer science and chemistry. Years of medical training and practicing emergency medicine exposed me to a lot of computers but no programming until I recently was involved in designing the tracking board software for our emergency rooms in our system. I had to transition from an assembly mindset to c#. I jumped into SmartThings pretty quickly and dove head-first into webcore. I abandoned ship on SmartThings when they reported that webcore was being phased out. That's when I jumped to HE. The majority of my automation is centered around webcore with a few rules in RM. The WAF is my limiting factor. She moans every time I start a new project and just does not understand the concept of debugging.
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The biggest problem with HA is a very fussy specs and standardization.
The result is - very poor device interoperability.
This leads to enormous effort for drivers customization.
Etc, etc, etc ...
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I would add the market over-hyping the capabilities and ease of installation of home automation while downplaying the complexity beyond the simple "light on/off timer" setup. Also the plethora of cheap crap out there that may or may not work with a user's system and breaks after a few months.
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