There was seepage and required tuckpointing repairs noted in the basement (the basement is unfinished and used for storage / laundry / mechanical purposes) - is this something I should be seriously concerned when thinking long term and what might these issues point to?

Get an inspection done and check everything from mechanical, roof, electrical.

Rent to own of a primary residence is illegal in most state without special licensure, and some states refuse to create a licensing mechanism thus making it illegal by fiat. 17 states consider lease with option to purchase a disguised credit transaction and may or may not offer licensure for this method.

That should be basics of the mechanics on how to bring the losses "forward." 

It doesn’t take much time or mechanical knowledge to learn about mechanical systems in this industry.

To ignore roof, appliance and other large mechanical replacements in amortized annual expense estimates leads to unrealistic yield assessments.  

Engineer (structural, mechanical, electrical, etc)7.

I plan on placing great emphasis on its rentability and the potential to acquire positive cash-flow.

I'm a mechanical engineer that is striving for financial independence and see real estate investing as a great avenue for it!

The two biggest things I would point out that I don't think got enough emphasis above.