Best game plan for turning my cash into cash-flow?

[Jonathan Studdard]

I am trying to put an ideal game plan together to begin my journey in REI. My goal is to use the cash I have to achieve enough cash flow to cover my living expenses within a couple years (if it's even possible). If I can achieve $5,000/month, then I will have financial freedom. I have about $100k I would be comfortable using, which would leave me more than that in reserve for a rainy day. I don't have a handy "DIY" bone in my body, but I have cash and I know a lot of people in the blue collar fields of construction, etc. I also have a couple close, like-minded friends who don't have as much cash, but want to get into REI as well. I know that a rental portfolio generating cash flow of $5k/month does not happen overnight, and I fear that I lack the cash to really achieve this before I would run out of capital. This has led me to conclude that I would have to make some money through some flipping along the way to supplement my working capital. Is starting out flipping my best bet? Or is it possible (using more of my cash) to purchase an existing rental portfolio (I have 0 actual experience) that would cash flow this much off the bat? Luckily I'm in no rush, but I don't want to see my money dwindle away to inflation or burning a hole in the wife's pocket. ;)