I have one cloud-based custom integration (I know, yuck) that takes approximately 2 minutes longer to load than any of my other integrations. When I restart HA, everything sits and waits for this integration to finish loading before ANY automations work. Why is HA crippled until the last integration loads?
Because your automations may depend on entities provided by the integration and it could lead to unpredictable behaviour.
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That makes sense. But why not disable only the automations that are dependent on that particular integration until it has loaded? And let everything else function.
Can you maybe describe what bothers you exactly with the long restart time?
For me personally, it wouldn’t cause problems to wait 2 minutes, since I don’t restart that often. So maybe some more information about your situation can shine more light at the issue 
Simple. My wife has a superpower: The ability to press light switches the exact moment that I restart HA.
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Its similar when using the Android ADB integration with your TV off. That removes actions and adds a fair few minutes to my restart times if i reboot with my TV off.
Whilst i believe this is more down to specific integrations than core ive added my vote.
My wife is similar, she is great for testing my automations against as she will walk straight into the situation i didnt account for!
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