I also love what I do and am not currently looking to replace my day job but instead use REI to enhance our digital nomad lifestyle while building long term wealth.

@Justin Ringer Perhaps you've seen it, but this is a more recent article from the Montana Standard that may be of interest to you: Real Estate Professionals Say Butte Market is Healthy.

Is the person whose health is deteriorating the Trustee of the Trust that holds title? 

The question is how much of your current life do you want to sacrifice to have a nicer lifestyle later on.

You destroy any and all obstacles in the way of your success, because your success means a healthy prosperous life for your wife kids, dog AND goldfish!

I am a healthy 47 y/o self employed contractor and self manage my 3 properties.

While saving may not be a lifestyle choice I see it as a lifestyle and not having adequate savings is a major red flag. 

She was 45. 10 years later she was looking for work.Your health is a good investment.

@Nathan Hagge, kudos to you for working out that lifestyle!

Once you have exhausted your current income and your cash flow is adequate to support your lifestyle; at that point, you can consider leaving your job.