If you let fear guide you, you will lead a fearful life. If the numbers work, then they work. Don't get stuck in analysis paralysis.
I wanted to JV a 10unit, but didn't have the capital that all those that considered doing it wanted me to have more skin in the game. But with poor credit, no assets worth flipping and limited income I am working up to it. I'm wholesaling the deal now, but I'm going to continue putting in work to get there and helping the person go through the process because I want her to be successful. And if she's successful, then I'm successful and I will learn how to rehab and rent a 10unit. So the next time I can bring more to the table.
I guess when I get there, I'll let you know how I feel.
But back to your question, every time I train a new soldier, teach someone about real estate, and show someone how to analyze large volumes of data(I'm an analyst by trade) then I think what if I didn't do that and just leave it to someone else. Then I think, that if I didn't do that then someone else will. They will step up to the plate, because you couldn't.
What if sets in, that's the worst feeling I've ever felt. I would rather regret than think about what if. But that's me.
I hope this helps in some way. If not then, I've told you my feelings for nothing! ><