If I were to go through and respond to each part this would take forever. So I'll grab the highlights.
First of all, thank you all for the kind words, thoughts and taking the time to share them.
On the, "do you know what you are getting into with house flips?" Yes, I over think EVERYTHING before making up my mind. As I mentioned, I have been doing the work for a long time, dad was a contractor, I know it's dirty, grungy, downright awful work at times. I also have dealt with the permits and that bs for a few years as well. The flipping regulations aren't actually legally binding in most states, but I digress on that portion. There really isn't anything in your way here persay, there are actually programs looking for "good" investors to help rehab communities more than regulations stopping it. Also, the TV shows should be required to put something like a parental warning on before and after the show. They make it look like you can flip a house in 48 hours with some pixie dust and paint. I probably could if I had a 100 man crew working 24 hours a day and no "real" work to be done, but that's just not the case. I'm not thinking of flips as a paint job, floor and maybe a counter top. That's wonderful for making extra money when you sell a track home, but reality is, you have to find a disgusting deal to ever have that happen.. which is not going to happen without pure dumb luck in this market.
I'm extremely lucky to have a great wife who also makes a solid living and could honestly support us completely, so my family risk is minimal. I got one thing right!
The biggest stress to me is the fact that I haven't done it. I have the knowledge, but that's like saying college kids know the same thing as their instructors. I know I'm likely to make a few mistakes on the way. I'm also not great at asking for help, so that's going to be an obstacle I have to overcome. I do think I would prefer the stress of the unknown more than the "security" ( why is this conversation happening again?) of a job. Because without risk, nothing ever advances. I live for that and can die for it I guess. So in that respect, I believe I have the mental ability to handle a business life.
It's nice to come here and see some people have made the jump and it's worked and to hear the assurance of the fact I could go back to work if need be. I appreciate all of that!
Right now, I own the house (well in the process of it) so I'm going to flip it. I'm keeping my mind open to taking a job if the opportunity arises that I can't refuse. I need to find avoid the mistake of chasing the money and go for something that lets me do what I'm good at and passionate about. On the business side, a consultant role would really be my best fit, yet I have tried to make myself do Sales for the longest time. I'm good enough at it, but I really don't enjoy it, with 30+ years of work to go, I can't continue on a path that makes me unhappy about it each day.
My unofficial position at the moment is to get after the flip and see where life takes me. It's been a week of freedom that has really been quite helpful for me in reflection of my past few years and looking towards the future. I ultimately know I will have to be in a position to run my own daily operations to be satisfied. There are so many avenues that allow for that, it's a matter of finding the right one. I feel like everyday I'm finding out more about what I want to have as part of that and getting a clearer image of what each opportunity will present and from that, getting closer to defining the path. You all have been very insightful on some of those pieces, I can't thank you enough.