If you need to get it rented fast, a great property manager would list the home for $2100 (below market) and get several quality applicants competing against each other to drive the price up to the max so you don't risk vacancy by starting out too high and gradually reducing to find the sweet spot.

Along with your list, consider building a local team in each market to make managing your STR easier.

I’ve built strong relationships with agents, contractors, and other investors in the area, and one of my contacts informed me that the owner was considering selling but hadn’t listed the property yet.

I did check Loopnet and it's all listed for sale by brokers and agents, so I don't think it is off-market -- right?

In addition to Turbo Tenant, I would suggest that you have a local Realtor list it for rent. 

I’ve built strong relationships with agents, contractors, and other investors in the area, and one of my contacts informed me that the owner was considering selling but hadn’t listed the property yet.

When applying for loans, do not list your wife as the co borrower and vice versa.

Hi Jessica, I would suggest getting a propstream or any other lead generation account, finding cash buyers who bought similiar properties to yours in the last 3-6 months in the area of the properties you are looking to sell, skip trace then cold call or cold texting the list. 

I recognized your name from the list of people attending the Westbank REI meet up tomorrow.

The strategies you listed are drastically different from each other.