Then there's other factors to success especially in a heavy lift like this, some of the most important in my opinion are Being on site regularly to manage the contracting processHaving a lot of cash reserves - 'a lot' imo would depend on how thorough your current bids are and how old the property isYou mentioned it's bleeding cash now, whatever your timeline is for the property bleeding I'd double it and see if it still makes sense. 

As a sideline to a regular local self-managing small landlord in my position, oh, very much so.Anyway, Steve, I'll send you a connection request.

What you've shown here is not really a cause for concern in my eyes, however I see much worst conditions regularly.

Property Management Company we work with right now to manage is fine with regular rental but I am having hard time working with them on student rental where some of the regular renting rules don't generally apply. 

Begin small by making regular contributions to build your portfolio over time.

For clients you bill regularly, you can schedule invoices to send automatically, so you don’t have to do it manually every time.

There are good and bad tenants in each category.No one can logically say Section 8 tenants overall are better than regular tenants.

Things change regularly and I would truly be interested in hearing from investors "everywhere". 

I'd focus on getting a better property manager, their job is to shield you from most of these headaches and to prevent them in the first place through tenant selection and doing regular property inspections.

If after adding the additional monthly recurring costs (electricity, gas, water, internet, insurance, lawn care, snow plowing, etc.) to the standard long-term costs (Mortgage, taxes, regular insurance, etc.) the property won't net at least $100 if I can get the average rent I see on FF for that area, then the property isn't worth more investigation.