Anyone have any experience with placing a flat billboard on the side of a building in Philadelphia? If so, can you send me DM. Thank you

While that kind of income is not a deterring factor, when I looked over the terms of service many big red flags came up.

This is usually done to increase your rental income but it comes with a price as you are finding out.  

Another variable in the amount of rent that a Section 8 tenant can pay is HUD limits their rent payment based on the amount of their income. 

The house I will get is in a lower income area, currently worth $95-100k, and she still owes about $25k on it.

You can Host Finacial revenue tool to get an average of the income.

While institutional lenders would probably need a number years proof of collections before considering the income from the wrap, private lenders, such as myself would look upon the situation more favorably.  

This aligns with my interest in passive income.

Could you put it on a CC and pay it off within the billing cycle with either your income or selling some stock if absolutely necessary?

I would like to build a duplex on it for long term rental income.