If you already have income and are eligible to buy real estate; your DTI will not prevent you from acquiring a house if you are purchasing a cash-flow positive investment property.

A favorite trick of sellers is that for one or two years before they put their property up for sale they stop doing any preventive maintenance, and only do the repairs that are absolutely necessary, in the cheapest way possible.  

One big key you left out that will prevent anyone from giving you accurate input is, what will the unit rent for each month?

@Daniel Mohnkern Tree roots will grow back, so as preventative measure you might want to rotor the roots on some schedule. 

I'm on that same track and think it can be good when you find a place where the housing prices are high enough to prevent a lot of purchasing and the rents are high enough to turn a profit in a 20-30% down scenario.

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In the event if a default, the second could pay off the first or work with the first lien holder to prevent getting wiped out in a trustee sale.

Lately there has been much talk about high rents preventing people from living in the better areas of town and they are throwing blame at everything from gentrification to greedy landlords.

One of the best ways is to make sure that your option is "assignable", which means you can sell it.This gives you flexibility in case you have to move or you can't get financing.Another way to protect yourself is to "record the option" at the county recorder's office, which basically "clouds" the title, preventing the seller from selling the property.Legally, properties can be sold "subject to options," but just recording your option to purchase will help protect your contract with the seller.Another way to protect yourself as a buyer on a lease to own is to use a third-party collection company, like www.notecollection.comThe note collection company will take your money from your bank account, and pay the mortgage company their PITI payment that the seller is supposed pay every month.