Todd,
My immediate thoughts are -- Quit. You're done! Congratulations! Great job! I completely get your fear of letting go of income and insurance. I had an easy time quitting (I was self-employed so self-insured anyway), but a much harder time convincing myself to just enjoy my income -- it took me two years to convince myself I could afford to buy a horse. (I am now spending $1200+ per month indulging myself, and I am so glad; if I had waited another 10 years I am sure I would not have done it.)
Your numbers are alot like mine, and I find no problem living off just RE. I still have two kids getting ready to go to college (one next year - one in two years.) I am putting them through private school, and their college money is saved and ready to go. Health insurance for me has been affordable. Get a quote through the healthcare exchange ... you might be able to get a better policy that provides more coverage?
My rental portfolio yields about $13k/mo, I have one tiny mortgage left (I owe $18k on a $350,000 triplex that grosses $3150/mo -- my payment is $750/mo; will be gone before second child goes to college.) I sold many houses over the years. In the past 3-4 years, I started paying off all my mortgages, and buying with cash. NOTE - I did this solely for peace of mind, as a purely personal choice -- I began buying at 100% leverage on HELOCS and mortgages, and I still keep a HELOC open. Debt truly worked for me; now it just doesn't fit my comfort zone. I would have MORE money if I took on more debt, so I am not bashing debt! I flip, too, using cash ... but I tend to hold for a year to keep my gains in the Long Term range.
So, based on what I did, one thought is to sell a single, highly appreciated property. Use the proceeds to eliminate all your mortgages. You'll have the cash cushion you want on hand. And you can easily step into another investment when you're ready. They are always out there; clearly you are very good at finding them and doing them well!
I agree with the poster who said your taxes may go down substantially. My current flip I bought for $ 300,000 cash, putting in around $75,000 cash and I believe I will get out in the $550,000 range. I am holding it for over a year, so taxes will be 15%. This is an "advantage" of having no income except real estate ... your tax rate will go down.
Good luck in whatever you choose. Put yourself and your family first; you have worked hard and deserve to enjoy it while you are still young and have your health. I think you are in a solid position, and should be safe and secure.
My question for you --please share with me your favorite dividend stocks, and any more crowd street or similar passive income opportunities. I want to simplify further; love to hear more insights from someone doing so well in that vein. I am very interested in passive investing now.
I truly think you will be fine. Best of luck! Excellent work!
Karen