@Chris Collins
If you love what you do for a living you'll never "work" a day in your life...or at least i've been told!
Having the ability to freelance your current profession should give you a bit more confidence in your ability to walk away, but hopefully you won't have to play that card unless you want to, on your terms!
If it wasn't for paying for professional property management, i'd be close to matching my W2 income, just not my full benefit package.
I'm 52, earn a 6 figure income, raising two grandchildren....don't want to work another 10-15 years and miss out on spending time with them before they grow up and abandon us, lol. However, losing company sponsored health care at my age while raising a family is scary! I have reached my earring potential at my job, and the only bonus for me is working overtime. Ironically, i'm at work right now, got called in to cover someone who's ill.
My wife and I just finished the purchase, rehab and repositioning of a 20 unit multifamily, and I want more! I'm also afraid that giving up my W2 income would greatly affect any large real estate deals, and at this point that's really all I'd be interested in. Getting my wife on board is another thing....she loves my job, steady, good income, good benefits...it is a GREAT job, but it's still a JOB!