Help with achieving a Goal

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I'm setting a goal to have 10k/ month in passive (doesn't have to be truly passive i'm ok managing the properties myself) income by November 2016. I have 500k liquid to work with. 

Real Estate/personal background info. I'm 28 years old I live in Biloxi, MS. I've rehabbed and successfully flipped two apartment complexes (57 units total), bought and sold a courthouse step property, and had a few other real estate ventures that failed. Long story short I'm fairly comfortable at this point in searching for single family or multi family deals to buy and flip but what i'm looking to do is effectively be able to retire if i chose to do so in the next 12 months. So i'm looking to start buying and holding some things. I'm in the planning stages right now and trying to map out what i'm going to attempt to execute over the next 12 months to make this a reality. 

I have some questions.

1) Is my goal possible? I understand my market is different from your market but what I want to hear someone who has experience say is. "Absolutely, or it's highly unlikely". Absolutely but it's highly unlikely is acceptable as well. :)

2) How would you spend the money? Can someone give an example of why paying cash for 5 different SFR @100k would be a BIG mistake vs leveraging the money and buying 20 SFR putting 20% down on each.

3) Does anyone have a spreadsheet or a link to one that gives you cash on cash return after you factor in depreciation and interest paid etc..? 

I feel like overall what i'm asking is difficult to answer since the market i'm going to be investing in will differ from yours but I think it'd be very helpful to hear what some of your plans would be in your current markets with 500K cash to work with. What would you do?  Any feedback is greatly appreciated.