I think the instructions are fairly clear:All of the gifts made during the calendar year to a donee are fully excluded under the annual exclusion if they are all gifts of present interest and they total $17,000 or less.The basic exclusion amount is lifetime - what you can give away under the annual cap each year together with what you leave upon death.The IRS keeps its options open: If the donor doesn't pay they can collect the gift tax from the donee.I think that addresses all of your concerns.

Sell one or so each calendar year vs all at once to minimize the tax hit?

Many of these goals are private to me and my wife but a couple of them are relevant to the BP community.  1) I plan to post a minimum of 120 times this year with a minimum of 10 posts in each calendar month. 

And as the calendar records the years, it becomes increasingly evident that the easy way rests hazardously upon shifting sands, whereas the hard way builds solidly a foundation of confidence that cannot be swept away.Harland David Sanders

These are challenges we all have.Show me your checkbook (and calendar) and I will tell you what you value. 

STR I can look at the booking calendar and see it will be close to 50% of normal.I am expecting to come out of this with significantly less net worth than prior to the virus. 

(c) If the court determines that the tenant’s inability to stay current on the rent is the result of increased costs in household necessities or decreased household earnings due to the COVID-19 virus and the court finds that it would not be an material economic hardship to the plaintiff and if the court determines that no cause exists after review of a timely response from the plaintiff, then the court shall make the following order:(1) The tenant shall remain in possession.(2) The rent for the rental property at issue shall be reduced by 25 percent for the next 12-month period.(3) The tenant shall make monthly payments to the landlord beginning in the next calendar month, in strict compliance with all of the following terms:(A) The payment shall be in the amount of the monthly rent as adjusted pursuant to paragraph (2), plus 10 percent of the unpaid rent owing at the time of the order, excluding late fees, court costs, attorneys fees, and any other charge other than rent.

You can put the house on multiple booking agencies and sync the calendars so that it's on multiple platforms but you don't overbook.

I have been researching the topic of short term rentals in downtown Chicago and would like to find out if anyone has any hands on experience with this and can provide some additional insight.Target audience would be vacation and corporate rentals.Marketing is pretty well covered by sites like AirBnB, VRBO, etc and currently posted properties have their calendars filled at approximately 50-80% rate. 

Zuck probably had to book time on his calendar a month in advance to take a few hours for surfing.