Sure, about one in 2000 times, by someone experienced enough to recognize a very unusual situation, having the capacity to act on it, having the financial strength, experience and tract record to be able to attract the needed capital, having the knowledge and ability to structure the deal, having the ability to manage and or reposition the property after purchase, and having the capacity to carry the negative cash flow until turning the property around or obtaining lower cost financing.  

I manage hundreds of rentals, thousands of renters.

Have a frank conversation with the property manager. 

It depends on the property.... is it value add where there's also a construction component or merely a management improvement opportunity?

@Kwanza Price tips for managing contractors:1.

Do you recommend making relationship with property management companies?

Since you mentioned you're working 9-5, I’d suggest look into turnkey rental and considering property managers to help manage you’re property.

Quote from @Joy Daniels: I manage short-term rentals in the Sarasota area, and I'm always looking for innovative ways to boost occupancy rates year-round.From your experience, what marketing strategies have had the biggest impact on keeping your properties booked?

I am a real estate broker and property manager based in Clarksville, TN and I specialize in working with investors.

If you're going to run a successful business renovating houses, ultimately you being proficient at/and or managing said proficiency in estimating will be a crucial part of your underwriting.Google "how to estimate house remodeling" your hard work will be rewarded.