However, due to short seasons, and more mild winters, I'm struggling to think even 3-4 years from now that I'd pull anything more than $50K a year in rentals.Bills / property taxes are about $12,000 a year.The thing is, being single, and not really dying to work in this area (small town), I'm feeling rather stuck, as is all the equity.I'm currently not working, but very much want to move back to Chicago, a place I love, and start buying cash flowing properties.I'd suspect I would have about $900,000+ after all is done if it sold at $950K, considering the vast array of other things I've accumulated (wood splitters, machinery, tools, MCM furniture, rugs,).

Your path to accumulating money through real estate will need a great deal of patience, learning, and smart preparation.

My primary interest is buy and hold property accumulation.

I'm a part of the mastermind headed by Kyle, so I am aware of his mentality, personality, and track record when going into this deal as a limited partner. 7% preferred return accumulated over the life of the business plan.

Most of the water has nowhere to go during a heavy rain and drains toward a walk out basement "pit" this is where the water is accumulating.

Not just wipe out what you have now but wipe out what you might accumulate in the next 10,15 or even 20 years. 

I'll just speak for me - my wife, kids, friends, neighbors do not care AT ALL about the knowledge that I feel I've accumulated.

some manage to jump after a single deal, others accumulate dozens of units first.thoughts?

I plan to have it forever and accumulate properties as I go.What advice do you have for me?

In a normal life insurance policy, yes, cash value accumulates slowly and steadily.