L.R.
I have to say up front I am not homeschooling so I don't come from that perspective, but one thing to bear in mind is that eventually your son will go to college and you and your husband will retire -- you do need to think now about how ready you will be to pay for college when the time comes, and whether you are planning and saving now for retirement or other financial needs. If working would help substantially with those issues, that's a factor to consider. There certainly are other factors involved, including the educational benefits you find in homeschooling, but if you don't already have a specific plan where you are already saving for college and retirement, you need one, whether you return to work or not.
Also, you mention that you have homeschooled for five years and he's entering sixth grade, so he has never been in a traditional school setting except maybe for kindergarten--? Is that correct? One thing to consider is that your local schools (public or private) may be different from what you expected or experienced when you started homeschooling. Again, I am not against homeschooling and know a variety of people who have done it for a variety of reasons--some have removed kids from school as late as high school to do it, while others did it through elementary but put their kids into schools in middle school onward. It sounds to me like maybe you need to do more investigating about what the schools are like right now where you are; they may serve him very well now, even if they had issues earlier, but you would have to do some research and make visits to find out.
Also, if he is entering sixth, is that the last year of elementary or the first year of middle school in your school system? If it's the latter, that may provide a natural transition point that is a good time for him to go to a school if you want that; he would enter middle school with other kids who are coming in from many different schools and meeting new kids for the first time, just as he would be. If he enters elementary in sixth, the kids would all know each other already for years but if it's middle school, they are more in the same boat as far as meeting new kids and being in a new environment together.
You mention "if I can find someone to continue what we are doing as far as homeschooling" but isn't that in effect placing him with someone else as his teacher, as if he's in their "school"? Check your state laws on homeschooling because they may prohibit simply placing him with someone else who is also homeschooling their own children, if one of his own parents is not one of his teachers any more.