Other things I like to look at is age of all mechanicals, roof, etc as there may be a need to replace, repair these items sooner than later. 

Even on a newer house that number is going to run you at least $150/month.As @Patrick Liska mentions there are several items not included on the list

Be aware that if you've got a tax loss (even if you have a cash gain), you'll have no tax liability in the state where you own rentals and, therefore, no filing requirement.  

The clog yesterday needed toilet removed.My question is, do you think it makes more sense to bill the Resident directly after it was unclogged, or wait till the lease is up and itemize the clog charge as a deduction on their security deposit?

In the state of Hawaii, I have a duty to mitigate my losses by re-listing the property once I have possession on Dec 13th.

You may want to consider a strategy such as Cost Segregation to help lower your taxable income and maximize current year deductions to generate a loss that will carry over.Third, You NEVER want to hold rentals in a corporation.  

The key is understanding how it works in terms of it's structure...Corporation -> Workspaces -> Apps -> Items -> FieldsI will say that while Podio itself is great, you really need to integrate GlobiFlow so you can create automations to help control the flow of your data and create tasks to run your business on.  

If you have a cash gain, but a tax (paper) loss - usually due to depreciation - the losses you can take through an S-Corp may be limited.  

You should be billing him for all the broke items you keep repairing also if it is not normal wear and tear.I think you will be relieved once he is gone!

Capital gains are for an asset that you intend to buy and hold, not fix and flip or even build from the ground up.The IRS says this:The following transactions result in gain or loss subject to section 1231 treatment.