You need to discipline yourself and your family to live beneath your means.

The issue I’m having is that the water pools beneath the wood deck and cannot drain or evaporate.

Just roller covers, trays, tape, caulk, screws, shims, etc... can be hundreds of dollars in the project.

Turns out the tub had been leaking for years and rotted out the subfloor and joists beneath it. 

I would put down plywood shim as needed and then then the tile board. 

You make your money when you buy, not when you sell.ControlOne of the biggest advantages to investing in real estate opposed to any other asset class is that you are in control of the land, the mineral rights beneath the land, and the air rights above the land (a form of God's money).

Just purchse one of the back pack plastic garden sprayers and really soak the roof.I am assuming firbrglass/asphalt shingles not wood shingles.There is also a zinc product that works well and if you are installing a new roof you can purchase zinc strips that are installed beneath the cap shingles with a small 1/2 inch band showing it will keep the black stains from starting.

The reason the big brokerages invented  the notion of CapEx beneath the fold is precisely because it is extremely difficult to make a building look good on paper when accounting for al of the true operating costs.  

turns out the flange was completely rusted out,  and I needed to replace the subfloor beneath the toilet.I addressed all these issues,  and the tenant was very happy.  

Vent pipe boots - water gets in around the vent pipe (at the roof) and follows the pipe down until it runs laterally, where it then drops onto whatever is beneath.