I realize that this may need some light fixing up here and there since it's not freshly rehabbed.

I am in a position pretty similar to you, (freshly) 25, finished up college a little over a year ago, and looking at getting into this in the next 6 months and move to the Winchester, VA area.

I found this very useful on the forums that @Christopher Phillips a Real Estate Agent from Garden City, New Yorksaid "1031 can't be used for personal property.

I love the Westland / Redford /wayne /garden city area.

Plus you can listen to podcasts anywhere, whether you're driving to work, running, working in the garden, walking down the street, etc. 

I liked the tenant he found and decided to just do a fresh lease with him.

I am thinking maybe the owner would be happy to receive some rental income and instead of it being a money pit because he has to pay some employees such as a manager and gardener to take care of it while it sits empty and for sale. 

New windows definitely have more of an appeal to the tenant because they offer a fresh look and will reduce your energy expenses. 

I am fresh in the wholesale real estate game and would love pointers, advise, maybe even possibly meet up with local wholesale investors to chat and maybe eventually co-sale.

Roof should be fine but it is a simple garden home a-frame house. 1,300 square feet.