Also, North Linden (having so many tradespeople) has a reputation for being harder for contractors to make money in..

Biggest recommendation I think you will receive consists of becoming an agent while you are attending college OR working for a property management + contractor. 

With that being said, based on what I have been advised for my own situation as a landlord, as well as my own research on the subject, I do NOT have to issue 1099's - even if I pay one of my contractors over $600.

From your recommendations on PM, contractors, banks, inspectors...etc...people will see that you know the area, recommend good, solid and reputable companies and will keep coming back to you to purchase the property from you. 

I am looking to partner funds with friends and family in order to lend to a contractor partner, either as straight debt financing for acquistion and repair costs, or a combination of debt and equity partners, participating in profits after resale.  

:does this apply even if reported net loss in my federal filing after accounting for mortgage interest, depreciation and  expenses for maintainence and when acquiring the propertyi didnt file a city of cleveland return nor state as there was no net income Yes, you still need to file.City of Cleveland taxes are collected by the CCA (one of two contractor organizations that deal with municipal tax in Ohio, and definitely the nastier of the two.)

Do you buy the windows and find a contractor to install them?

I would set up for a contractor to do a scope of work with you or at least have an inspector walk the property.  

My lawn service, contractors and pest control guys tell me if pets or other shady activities are happening at the property.

But if anyone knows any good contractors for a minor concrete job in the back to repair some stairs and garden holding wall would be interested in that.