Problems arise when you run your own server, because of fairly detailed authentication settings. If you pay a provider to run their servers, they take care of that.
Of course, it's important to keep backups of everything (configs, logs, mail, etc), and test. Just slowly port everything over, as you gain more confidence that your not missing anything. Most email providers also will let you put a rule in place that lets you bounce mail to both addresses.
Where you run into problems is when you do what I just did, I was using Google Apps, then Outlook.com with a custom domain and decided I was tired of giving other people access to my data - since I have a decent business-class cable connection at home including a static IP I bought a couple GroupWise licenses for myself, my wife and my daughter and moved our email in-home where all our data sits comfortably on my FreeNAS storage array. Since I rarely send email, and my home IP is 'unknown' to any IP reputation services at the moment getting past spam filters will require some time. It's a non-issue for me, it's a personal email account and I can tell my friends and family to check their spam folders the first time I contact them to whitelist my address, but it's not something everyone wants to deal with.
Tho FWIW I use Postmark to do my email delivery because then at least I know my email will end up in the inbox of the recipient vs their spam box which my hosted server was having problems with.
Edit: I'm not even considering running my own email server; I know that's a full-time job. Just something like forwarding my custom email to my Gmail address, which is the type of thing I've heard the aforementioned scary stories about (though a quick web search isn't turning up many such stories).