I’ve been manually scouring Zillow/MLS for deals, but it’s time-consuming, and I’d love to streamline this.2.Has anyone experimented with using machine learning models (like classifiers or regression models) to rate properties based on their condition from MLS listing photos?

What type of properties are you seeking; SFH, Condos, Townhomes, Duplexes, 3/4 plex, ect.  

Quote from @Matt Cook: I would really get with a realtor that is in the area of that property and that sells a lot of homes to comp the property on what it can sell for after the remodel.

I searched for properties that stay on the market for a long time.

I would consider getting out of property management and getting into cleaning IF you think they are doing better than you . 

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

as others have stated, if a RE agent does not believe they can sell the property, find a different agent that believes they can sell the property.  

I recommend starting by contacting the county’s property tax office to determine if they are open to discussing or reviewing an appeal for property taxes.

Property management is also in place.