Maybe 10 years ago or so I remember it was a pretty big issue here, when they capped real estate loans on owner occupied properties at 12%. 

@Bradley Cumming one issue with your plan is that you need "good" credit to refi!!

Good  tenants should have no issues with a M2M lease.

Of course the answer to this issue if you close late in the year and want the full 180 days is to file an extension.For you it is irrelevant whether you sell and close the purchase in 2016 or close the sale in 2016 and the purchase in 2017.  

I have had numerous businesses through the years but it was serious health issue and the realization that disability social security payments would not allow me to live that made me want to build a successful RE portfolio.

Our lender also informed us that the biggest issue that raised the red flag and qualified the property to be in Below Average Condition is the detached garage which needs major repair.Our dilemma:Our lender gave us the option to buy the property all cash and refinance instead of it being considered a purchase.

If you have " small maintenance " issues and need to get a loan , whats going to happen when the tenants dont pay ?

I am a new investor looking for cashflow rental properties, and from my preliminary search Milwaukee looks like a great option.I am from Southern California, so I am aware that you will need a local PM for this area, and thats fine.However, one issue is I dont know the good areas of town. 

Master insurance policy issues can be daunting as well.Seems to me that it would be easier to construct a duplex.  

I'd probably be content if they'd drop the price another $2,000 and was planning to ask for $4,000 off given those issues that need to be fixed.