I had similar concerns and this is what I did, and how it turned out.
[Sorry this is so long, but I spent way too much time making it this short.]
At about your age I was facing the prospect of going the management route or doing what I loved. I had been acting like a manger as a team lead but avoiding much of the messy side of dealing with personel. I was expected to move on up and take on the added burdens of full management and give up the hands-on fun (for me) stuff. Didn't want it, yet I saw what happened to 50 year olds who didn't move up. I didn't want that either. So, I planned an exit strategy, and left becoming more or less a consultant. I had an incorporated company(very important to be an employee of a company - not a freelancer) already set up and 6 months of cash put away before I left.
Here are a few key things that worked for me. They weren't really part of my strategy, but just came naturally, and really paid off.
(1) I really cared about the folks (mostly 10 to 15 years younger) I was leaving behind, and I wanted them to succeed after I left. I made it a point to mentor them, so they could survive after I left.
(2) I really cared about the organization and the current projects I was working on, and delayed my departure for a year, to make sure they succeeded and there was a heir apparent team lead to take over.
(3) I didn't tell anyone what I was planning, other than my wife, my dad (who had just retired) and a close uncle.
(4) When I was ready to leave, I went to my boss, and told him I would like to sit down with his boss and anyone else that they wanted to invite and explain exactly why I was leaving, what I intended to do after I left, and make sure that any rumors would be put to bed about why I was leaving. I reviewed everything I would say with my boss, and asked for any suggestions he had that might make what I said as painless as possible for him and his boss.
(5) The main points of that meeting were (1)(2) and (3) and I wanted them to know what I planned, before my peers and team members found out, so they could prepare to deal with any fallout.
(6) I also offered that I would stay up to 6 more months to help finish or transition projects, or I was prepared to be escorted by security on the spot to clean out my desk (which was official human resources policy at my previous job).
(7) The last and maybe most important point I tried to make in this meeting was that I was hoping not to burn any bridges, because they, the organization, the bosses, the team members helped make my career, and I didn't want them thinking bad about me, because who knows, they might even need me from time to time as a consultant. I told them that, I wasn't just thinking about it.
Now frankly, I figured I had a 50-50 shot of being shown the door immediately or worse. They probably thought I was a bit crazy leaving excellent pay and benefits for an uncertain future, but seemed to respect the approach I was taking.
Bottom line - they asked me to stay on for 6 more months and gave me a great send off complete with memorabilia. 6 months after that I was their consultant and they started outsourcing some development tasks, and now 12-1/2 years later, I still do work for them. Most of my income comes from other sources, but they are a dependable customer and the people I left behind have brought me a lot of business through their natural networking. My house is paid for, both my kids went to college, for as long as they wanted, and are doing very well in their chosen professions. I'm able to give away a substantial portion of my income to benefit those less who are less fortunate. So at least to this point it as worked out well by any measure.
One last part but not the least part of this story - (I'm pretty sure this will get mod'ed down because it cuts so much against the grain), I prayed this whole thing through, before during and after. I 'knew' this was the right thing for me to do and there was a right way to do it.
Full disclosure: Yes I'm one of those. In the early 70's I had long hair and was known as a 'Jesus Freak'. Now I have short hair (what's left of it) and I'm called a Gideon. IMHO, If you try something like this you will need a lot of faith, and it least in my case, it wasn't the faith in myself that mattered.
PS. In answer to one of your questions, it takes from $1500 to $2000 per month to maintain health insurance for yourself and spouse and another $100 or so per child, if you don't have a big organization or government program to subsidize it for you. It has always been my biggest expense.