Quote from @Chris Magistrado:The point he's making is that the agent must take responsibility for building and maintaining their business, and the Broker won't play much of a role.

It's possible tenants would fill basement with junk and leave it behind when they leave...

Your aim starting out should be to get the best reviews as possible and use guest feedback to make improvements as you go.

Then rent the bigger home out using a property manager, allowing her to possibly cash flow and maintain that asset and let it continue to grow in value.Encourage her to consult with a CPA or tax attorney to explore the best strategy tailored to her situation.

The transfer of bookings is possible because we're going with the same co-hosting/PM.  

Actually, it is possible do structure a 1031 Exchange on the sale of one or more relinquished properties and then using the proceeds through the 1031 Exchange to construct improvements on real property you already own.

If so the carrier has the right to deny any/all claims you make or if they want to be nice they will settle the claim and retro charge you the premium you would have owed having the proper policy in place when you started renting it out.Talk to a legit local agent and tell them what is going on and get them to run down all the exposures you have and what you could do to best protect yourself for the best possible premium.

On most any day you could find people walking dogs, or children playing in the area.

He’d likely play the role of buyer’s agent, contractor, and rental listing agent—something we successfully did last June.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.