I'd be terrified to even try it, without job placement assistance with an agency that specifically helps people with disabilities. Rather than explain the gap of a good many years in my work history, I'll let the job consultant do that for me. The employer will know I have disabilities before I even get to the interview, since all of the clientele of the placement agency do, everywhere from being in a wheelchair to being mentally challenged, and they won't be expecting otherwise.

For myself personally, it helps that I have physical limitations. The cane and the knee braces do the talking for me there, and it can be assumed that they are the reason I am considered "disabled." Also, being a woman, I could always fall back on being a stay-at-home mother and raising my children as an excuse not to have a paying job for X amount of time. It's a shame that doesn't work equally well for a man, yet. It should.