Repair/improvement and Safe Harbor rules

[Brandon Heimsoth]

Newish landlord here.  I have a couple items that need fixing at a property I'm managing myself and I'm wondering about the tax implications since they are higher ticket items.

Item #1:  The driveway

I got cited for a city violation as the driveway has a tripping hazard.  One of the slabs cracked/sank and there is a 1-2 inch drop off.  I got bids to replace just the one slab ($1800) or the whole thing ($2800).

Item #2:  Garage Door

The garage door opener has been causing fits and needs to be replaced.  It's ancient.  But, the door is old too so I would like to replace both.  I haven't gotten estimates for these but imagine it can replace both for $1000-2000.

I've read about this $2500 and safe harbor limits but would like details as to how that applies to my two scenarios.  If I can deduct all in one year, obviously that is beneficial.  Is it legit to separate things out to get under the $2500 amount?  Is the $2500 per item?  Is there a limit to amount of items per year?  For instance, if I wanted to replace all the windows in a house...I imagine that's going to cost more than $2500.  But, what if I just did a few at a time?  Any information would be much appreciated.