There is nothing perfect :(
My setup: I have my own webserver/host etc. And I use my own email addresses, the problem is sometimes the IP gets blacklisted, sure it's my fault because it's cheap and I didn't choose the best company, well that's the trick... because this sort of things can happen and I experienced these over different webhosts, including issues caused by an error during configuration (after being upgraded to a new server or account, etc) or someone just forgot to do something. Yes, paying for a private IP address helps, but human error on configurations can also affect you.
Hotmail/Outlook is what I use, I set up my mails for specific forwarding. Only use a few set of specific email addresses for sending. The service in my case has been great and I don't use the webmail (too slow and bloated). Sadly their filters and rules only work NOW on their addresses, not on synced accounts.
I had clients hosted at my webserver experiencing such issues, they relied on email more than anything else, but sometimes clients also do questionable stuff sending gazillion amount of emails to their lists (regardless of you making clear NOT to do this), so... depending on your company the mail service could be turned off, penalized, or limited to X amount of emails per hour, per day, etc. Depending their policies such abuse can affect only one mailbox but [u]usually it will affect the whole account[/u]. Sure, if you don't host clients then that shouldn't be a problem, right? sometimes your own employees can do these things just because...
BTW once I got upgraded for free to a new server with multiple benefits... but email went down. After struggling with tech support they informed the server had a X email per hour limit. Surprisingly by mistake it was sent to 10... 10 emails per hour, I mean, such things can happen.
A client used Gmail, and I didn't like it. I was constantly asked to help them with their mail, many things went straight to the spam folder, and sometimes their account would be temporarily paused because someone sent something (that's what happens when the company that gives you something for free has multiple "services" reading your mail or... "safety filters" whatever).
Some ex business owner used Gmail paid services (hosting, email, etc). It wasn't that much different.