It appears that you are thinking in the right direction as far as consideration of costs.
My priority would be health benefits, retirement and college funds.
I have been fortunate to have the best of both worlds. My late husband was in sales and I was SAHM with a business degree that I had been using at a major label snack food company in marketing.
For us, my hubby's employer was usually in another state which meant his CSR was there as well. His customers started calling me early on vs the CSR because they knew I would know what mile marker or where on a plane he was. I got in the habit of taking the orders, getting details and pretty much was my husband's CSR. I did all of his flights, hotels, expense reports, etc.
Move forward, we had an opportunity about 10 yrs ago to start our own business in his field. The experience I got working along with him... ( living on his salary alone, saving for retirement and funding daughter's college) was a vital part of where I am today. The major factor in having our own business was to secure health benefits through our company which we did.
There is NO way I could have done this and work full time with another company and raise our daughter, attend all of her events etc. I treasure my time I had with my daughter throughout her school years. True.. they don't "need" you as much for some things middle school and up but those years are hard on the teens emotionally and it was good to be around to be the sounding board my daughter needed. I was there for schedule planning for high school, college visits, college planning etc.
As much as I am home, my house if far from perfect. It s neat and orderly but no model home for a white glove test. Priority is my family.
In 2015 when hubby died, I was able to take on the company on my own which I could not have done if I had not been working alongside him all these years.
I have continued to substitute teach on a regular basis because I love the children. the $ comes in handy for fun money. I will begin year #18 this August.
All that said... the trick is to live beneath your means. Even though my hubby was brilliant and we were good planners, we still enlisted the services of our financial planner who really helps lay it all on the line as far as what we needed to earn, save, allocate for college, etc. We triggered health care to be a big issue for later on in life as we got older.
Your freelance idea is a good one and if you have the niche market for it, you might get your company set up.... make a business plan, use legal and tax counsel so you can be successful.. not just a fly by nighter. There is a lot of legal things to be aware of when owning your own business.
Bottom line, you have to decide what you want and what is right for you. Some moms prefer to be working moms and they are great moms. You do what is best for your family when you have the choice. Some moms have no choice in a situation like yours.
I wish you the best.