For example a leaking roof isn't very hard to notice if a proper walk-though was completed (discolored ceiling paint, patches, cracks, etc).

They had someone patch a hole, but now there is another one.

It took me about an hour to cut and cap the fresh water lines and cut and cap the drain line and remove the roof vent and patch the hole and redo a couple of shingles. 

The final one is in a small patch of this town that’s kinda funny.

That didnt include repairing a broken door frame and patching drywall holes from someone falling down the stairs!

This leads me down a rabbit hole:This is likely a very old house.It likely has some deflection in the floors (so you are never going to fill gaps and have the filler stay)Wood joints aren't true any longer due to shrinking of a 100+ year old materialYou have a number of different patches if looking across all of the pictuers.So, the last thing I would do is refinish this floor with a natural/stain finish.If it was a section 8 grade rental or similar, I would do a sand, vacuum, and paint with a flooring paint a brown.

I also just had my oil tank start to leak as it’s 70 years old, I patched temporarily but I’ll need to replace and that’s going to cost me a good chunk of change.

And you can always try patching your tub and cross your fingers.

Pumpkin patches are sprouting up all over our city with pumpkins aplenty and tons of festive activities.

There are important factors like how big the drywall patch behind the shower is, I assume that includes painting that patch which is another expense that wasn’t detailed but still needs to be done.