I recommend using a the HOLD spreadsheet: https://www.kellerink.com/resources/Easily lets you plug in the numbers and track cashflows and ROI.

If there's any questions about this, it is handled easily.

In some spots, I can afford it but January is a higher priced, very easily rented out time period and this person has requested a stay that leaves a single day on both sides empty. 

If that is a high-priority project and you feel strongly that it is the play you want to make, then I'd say today is a good day to go for it.If getting a property in our market is in the cards, you could easily accomplish that. 

If there are too many separate bills a tenant can easily pick and choose which is more important to pay when on a tight budget.

I can no longer easily terminate a tenant for things like too much clutter, too noisy, bringing unauthorized pets in but getting rid of them when notified, etc. 

I use this to easily have the data to give to my CPA.You can likely Google a good Excel template that you can use to customize as time goes on.I keep tenant info, AC filter sizes, trash pickup days, Magistrate info for potential evictions, Section login info in addition to the normal income and expense info. 

I streamlined quite a bit of the decor to things that are easily passed over with a duster.

Good thing about that crap is that it will come off easily and in sheets. 

I wouldn't give up so easily on it not being covered.