@Ryan Dickerson, while you will ultimately need to either make a somewhat blind leap or hope you can find a contractor that will walk your properties, one piece that I will add is: YOU need to know what type of finishes you are looking at, and understanding their material costs.I.e. are you going to do carpet, LVP, or true hardwoods?  

We added $40K-$50K refinishing the hardwood floors, removing wallpaper, painting walls and updating the kitchen & bathroom with new cabinets, adding granite countertops and creating a BEAUTIFUL dining room off the kitchen that was wasted space as an enclosed porch, and also added french doors leading out to a newly-built pre-finished deck we added so the new owners could enjoy their gorgeous fenced in backyard.

I have seen houses where the departing residents took kitchen cabinets, bathroom vanties, toilets, suspended ceiling and hardwood flooring when they left. 

The architecture of the house has been maintained with hardwood floors throughout, floor to ceiling windows and 14 foot ceilings (although a pain when accessing anything like lighting). 

Super nice house with nice landscaping , hardwood floors in great condition, nearly move in ready with new furnace/hotwater/ central air.

mainly cosmetic: stained floors, repaint, may need to replace carpet with hard wood, resurface cabnets, new shower, repatch water damage. 

As it relates to your roof, windows, doors, hardwood or vinyl flooring you should expect a serious issue to present itself every 5 years. 

I had never been to any auctions and never bought any real estate, yet prevailed at the auction, buying a 17 year old brick 3 bedroom house with hardwood floors, ceramic baths, and a brand new roof. 

There are things I know I will never look at doing myself: plumbing, electrical, roofing, installing hardwood flooring, bathroom remodel, and I'm sure many more! 

Discovered Bigger Pockets and a few other shows , and been lIstenIng to podcast episodes and audiobooks for a year while I did demo on walls, fixed termite damaged boards, fixed plumbing, resurface hardwood floors, etc etc etc etc (drywal) etc.