A lease with option could be the perfect instrument.

I'll give you a perfect example.

The other two sides to the property are in perfect shape.

Answered my question perfectly.

If you do not have the windows in perfect condition, chances are the next tenant may mark down the windows were dirty and then eventually the property owner will get stuck with the cleaning bill.

@David Harris oh sure, that makes perfect sense. 

The first deal did not perfectly meet my criteria, but after 2 months I felt I needed to just get started.

Do whatever you find best for you, we sub contract and divide labor as well as to outsource completely a project, I don't think there is a perfect way or a better way to manage contractors and sub contractors, what we do is that we make sure we have written contracts with all of them to make sure the scope of work is clearly defined. 

There is nothing to say that you wont strike gold and find the perfect tenant who pays enough to cover the mortgage, but it is much easier (especially if you don't mind college students) to charge a premium rent that cash flows hundreds of dollars into your pocket every month if you find a property within the city limits.

Helping others find their perfect home or investment makes me feel so overwhelmed with all the opportunities I'm missing out.