You cant report some income/expense on schedule E and carve out the interest expense from the line of credit and call it an investment activity and an itemized deduction on schedule A.

Expenses are an income statement item, repairs go to the assets of the balance sheet and capitalized.

I have sold many condos and have only had clients have issues with making interior changes if the change would negatively impact a neighbor, cause noise at inconvenient times or in the Pearl where there are can be a lot of restrictions on interior changes as they can cause structural issues (for example some buildings don't allow you to hang heavy items with maully bolts because of building envelope issues).  

I broke your question into the following items and will address each one as best as I can.Should you manage your own properties?

My back door doesn't openUnreasonable "honey do" list or items that can hit the back burner.......way in the back1.

Materials - could have saved on a bunch of items, now that we know where to go (we bought all the materials and also did the landscaping).

and looking at expected life vs cost of each item.

He's paid:1 - What ever cash he originally put in plus...2 - What ever losses he's incurred over the time of ownership (this would be "zero" if he's cash flowed the entire time, plus...3 - What ever he still owes...in this case $38,500.Since everything else is profit (cash flows), all he really has to do is sell it for more than the total of listed items 1 - 3 above, and he makes a profit....cash flows plus difference of what sells it for and what he paid (items 1 - 3) for it.This is one of the unappreciated advantages of owning rentals instead of flipping.  

Another item to consider: if your contractor can't afford gas to come do a bid, he may lack liquidity and cash to perform his services without coming to you with his hand out. 

The smallest items can help you document your files that this was a surprise and that you really did have the intent to hold for investment purposes.