If your real estate attorney specializes in closings, they might not be the best choice for entity structuring advice.You should be crystal clear on your own objectives long before you engage an attorney.

It appears that over half the houses in the Crystal Coast area have been removed from the sale market.  

Is it out of your job, vacation fund, retirement money added to a 401k, taking care of aging parents....You determine what the goal is and the answer will become crystal clear. 

Obviously, I don’t have a magic crystal ball so I cant perfectly estimate the cost of such expenses when they pop up but I can at least budget for them (which is the case in the example above).Regarding your second point, if the market is down, I could still hold the property.

I looked in my crystal ball to see when I thought that “break even” point with the tax would be and if I was comfortable with that.

Long term goal is single family buy & hold, and ultimately small multi-family buy & hold all in the NW suburbs (Woodstock, Crystal Lake, Algonquin, Huntley, etc), and to replace my FT income in the next 2 years.

@Brandon Carriere I understand no one has a crystal ball and maybe my math is wrong but are you telling me that you think my house could be worth 27000 to 40000 more in 6 -12 months?

I know of five methods that, have varying %'s of success:1 - Crystal Ball = 20%2 - Ouija Board = 21%3 - Palm Reader = 22% +/-4 - Card Reader = 22 - 23%5 - Fortune Teller = 25% (but I think they're just more experienced at guessing)...or, you can just do a really good analysis...and hope for the best.

If they know they are likely to not make rent payments on time they will not agree to a M2M lease.Chances are that if you accept a tenant with bad credit they will be making excuses and not paying rent on time.Make sure you make it crystal clear that the first time they are even one day late you will be non renewing their lease.

So if your 2% CoC investment also throws out 20% IRR (i.e. because of potentially insane appreciation), then it's obviously an excellent investment, but this is rarely achievable unless you invest in west or east coast and have a good crystal ball.Oh by the way, you can do all the above analysis without using "cap rate".