It's almost impossible to get deductible amount on some instances and owners are paying out of pocket.

If you have specific questions about property management, I'll be happy to help!

I’d specifically interested in flipping property.  

Quote from @Christian Styles: Potentially able to help you find someone but I would need to know specifically where the property is in order to know who to recommend.  

Feel free to reach out though if you have specific questions, it is fairly common!

Asking about the SW suburbs specifically, in the land of long sidewalks and big actual parking lots. 

The only information I had to go on was with the last Lender informed me so maybe it was specific to the company they were with.

Our buy box specifically focuses on vacation destination accommodations - including boutique motel/hotel, campgrounds, treehouses, cabins, etc.   

One of the most important steps you can take as either a startup landlord or seasoned one is to use a platform specific to property management as it will elevate your operation and save you tons of time.The good news is that nearly every software designed for landlords includes these features.

In terms of renovations it really doesn't matter much from a tax perspective.The bigger question is what are your specific investment goals?