I reward good tenants with stable rents, unit upgrades, and honeybaked hams for the holidays (not joking).Depending on the unit: By the time you factor in advertising, showings, taking apps, and prorated rents; basic turnover (normal wear and tear) runs equivalent to about one month's rent and goes up from there, in my experience. 

We're coming into a rough season to try to find tenants (i.e. winter in WA State and the holidays)... what would you guys do in this situation?

The disposition frees up both the capital loss carryover and the suspended passive losses. ( Sorry if this sound complicated, your CPA will understand if you hint this) S-crop can rent home form the owner and not report income but still get a deduction for the business:If the home is rented ( for meetings or retreat, or holiday party) less than 15 days a year, the owner can exclude the rent payments from the income.

This must be taking a toll to on yours and her relationship.This is why I never, ever do business with family or friends.When things go downhill, now you have to deal with seeing them at company holiday dinners, ugghhhh.I am not familiar with the NY landlord-tenant laws but know that, should this be processed as an eviction, what you are doing currently whether or not it shows up in court is not right and legally could work against you.Trust me, I really do empathize with you and your situation and it seems like this Brother in Law is really taking advantage of you, but don’t correct this wrong with another.Follow the legal process to get him out, talk to your wife to see if she can intervene at all, but it seems he may not listen to her either and just does not care.So my laughter is because I cannot for the life of me see how someone can think that this kind of behavior is right to do to anyone, leave alone your family.This man/boy should be ashamed of himself for putting you and your wife/his sister through this mess.After this, I suggest you be very careful about inviting family over for those extended stays that never seem to end. 

The extra person and her dog are visiting from out of state for the holidays and will be departing on Jan 2, they agreed to pay a $150 penalty for having an unauthorized pet in the apartment.

While many don't think having 5 military installations surrounding the city is a great tourism attraction, events like football games at the Air Force Academy and their graduation, as well as other holidays brings many out of town guests to be with near their military families year round. 

As an aside, the lockout keeps getting delayed because the holidays and now the weather.

I visited him over the holidays, stayed in his living room, and kept warm using a space heater to supplement the heating system.

I'd say that it's entirely normal to have issues renting a 3 bedroom unit around the holidays. 

As cities are starting to relax the regulations of ADU development a lot of homeowners (and investors) are thinking about ways to maximize their property investments.