Considering Flipping

I'm at a place in my life where I've realized that there has to be more. I'm going on 39, single, no kids. I have a good job that pays the bills and then some. I have a great family who loves me and supports me. I have an amazing boyfriend who is so good to me that I'm often left wondering what I ever did to deserve him. But, I've realized the hard (er...excruciating) way that work is bad for my health....primarily physical, but also mental. I mean this quite literally. In November 2013 I had my first back surgery. In December 2014 I had my second. It was a repeat of the first. One of my lumbar spinal discs herniated and then re-herniated. The second re-herniation was devastating. I lost feeling in my foot and use of my calf muscle, which prompted emergency surgery that resolved the indescribable pain but didn't change the loss of sensation or strength. This makes walking extremely difficult and endlessly frustrating. I have a desk job and you know what they say....."sitting is the new smoking." The idea of continuing on in the way I have for another 20+ years before I can retire and actually enjoy life makes no sense in my case. 20 more years of this will render my body completely useless.

I'm at a unique place in my financial situation right now. I recently sold a condo I owned in DC and have that money to reinvest. I have been a real estate junkie for the last 15 years, so I know I'll be reinvesting that money in real estate. What I am considering doing, though, is flipping a house with my boyfriend, John, who has flipped 11 properties and has made a profit on every one. Am I crazy?

I know real estate is volatile and I know that it's a competitive market. I also know that they say never to mix business with pleasure. All that doesn't negate the fact that this could be my way out of a job that is quite literally killing me. I'm also the type of person who is dying for a project, but wants a partner for said project. I've gone through the pros and cons in my head a thousand times and at the end of the day the biggest fear is it will ruin what John and I have. I know that these sorts of projects can breed conflict and resentment and it will be a very tricky landscape to navigate.

So, that's where I am right now. Still on the fence, but going to make a decision soon. Stay tuned.