Recommend consulting a tax advisor before moving forward with this.

For roughly $400 a year you can be a BP Pro member and it should be a tax write off as educational expense, but always ask your accountant, and use all the calculators infinite amounts of times.

If you own multiple properties, you can elect to group them together as a single activity for tax purposes, known as a "grouping election.”

If so, are they deducted from capital gains tax, or my normal income tax for the year in which I sell?

Lease the house would bring in about $2200 per month (minus tax, ins.) and so what would an Airbnb bring in?

Becoming an employer adds a whole different layer of rules/taxes etc in addition to that it might not be permitted by the Broker

They work on our accounting/bookkeeping/reporting/administrative aspects of our rental portfolio.

Also, at the end of the day, if you have budget left over, make a draw and enjoy that tax free money. 

You have limited appreciation and often the taxes go up later and shortfall the cash flow expectation.Rent-ready for you would also mean live-ready, but by having two residences and two short-term options when you are not there, you are creating a lot of upkeep and maintenance on both that will be very hard to manage.

Early withdraw taxes really hurt.