I suspect the reason for empoyers being very reticent to hire someone with an unsual past is due to all the job-protection legislation there is now. I'd love to take more risk on people with somewhat unsual backgrounds but, working at a university in the public sector, once we hire someone it is exceptionally hard - to an amazingly ridiculous extent - to fire them which makes it a massive risk.
As a result it is a lot safer to hire someone whom you know has been at a similar job and is working well there. While we clearly do need legislation to protect employees if it goes too far it makes employers extremely risk adverse because they know they are going to be stuck with whomever they hire.