I’d also be careful in updating too much because then you will find yourself in a hole that may not necessarily even add much value to your pocket in the short term.

Of course, there's a chance I'll fail and put myself in a deeper hole.

Longer explanation: I've been in contact with someone at an attorneys office who is appointed by the courts to look after peoples estates that are no longer able to themselves and have no heirs (mentally ill, elderly, etc) We take a look at this property that has literal holes in the roof.

Added bonus is when it comes time for them to leave you don't have to worry about them scraping your floors or putting holes in walls by trying to get a bed frame or a dresser out. 

@Jaysen Medhurst you were right alot of my numbers were guesses as the financials that were sent over from the realtor had holes in the data.

I just hate the thought of a brand new pristine roof being gouged with holes for a piece of trash to be mounted on it's virgin shingles. 

And if they have to drill holes for interior piers, you pretty much will have to replace the entire flooring. $$$$3.

More of an update: See the corner columns, towards the top on the left side of the building there was a hole in the building that they apparently forgot to fix when they did the roof maintenance.

The owner no longer lives there due to the extensive damage, including but not limited to a massive hole in the roof. 

Poke holes in my plan, tell me if I’m completely off the mark.