Points may also be treated differently between a primary residence and a rental.The $100k you are referring to is related to home equity indebtedness (home equity loan, HELOC) and that was removed with the Tax Cuts and Jobs Act.

To give you an idea of the extent of the projects, we ripped out the kitchen, removed a extra stairwell, moved a bedroom wall that was off the kitchen, cut concrete and added plumbing to make the bedroom a laundry room, converted the old laundry room upstairs into a bathroom for my daughter, stoned a fireplace, new flooring and carpet and ran all new electrical and piping to the new kitchen.

They are repairing a parapet wall, cutting in some doors, moving windows, removing an entire chimney and fireplace, etc. 

When he moves out it will actually be closer to cash flowing since I'm cutting him and his roommates a teeny break. 

@Peter FuentesLike many people who have a newly found interest in real estate investing, you are looking for the shortcut, easy way, the goose that laid the golden egg.I would try educating yourself about the industry, picking a strategy that you can make a billion dollars doing so, figure out how you can get the this point, make a plan of action and then follow it.I will tell you that from my experience there is no short cut, there is no magic answer, there is no easy way to make a billion dollars. 

Are there ways you or your wife can earn extra money or you can cut expenses to save faster?

They have boom lifts, man lifts, scissor lifts, golf carts, UTVs, portable lighting, etc. 

And don't even think about cutting down an oak tree! 

If so, cut your losses and sell.

Before the project thinking of what the investor can do personally to cut down on costs then in the end paying OOP for said repairs you thought you’d have the time to do...As long as you learned man, then I’d say it’s a victory.