listing a (now empty) rental to sell

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I don't know if this is the correct place for this:

listing a (now empty) rental to sell

My relationship with RE Agent Ann goes back 15 years when she saved my purchase of my home. We’ve become sort of friends over the last 2 years while she showed me several houses —easily over 20. I’ve put written offers on a few, but they came to nothing. The most recent was just countered, and I have not yet responded.

Until recently, I had the income to purchase without selling either of my houses. Now, selling my rental first is the best, maybe only thing to do, and though I prefer to give Ann the listing, I’m not sure that would be advantageous to me. Apparently RE companies are asking/requiring at least a 6-month contract. At least one agent asked for a YEAR! I don’t know that I can sustain an empty rental 6 months. Ann’s company also has a property management arm, but I would prefer to use the property management co I have now.

The management company (MC) I’ve used for 10 years also does sales. I like the management agreement and the working relationship I have with them. They would like the sales listing, too, of course. I asked them 3 times to have a sales agent call me about it. No one did, and when Ann was showing me the house I just put my offer on, I talked to her about listing my rental for sale, and asked her to get me comps on it, and listing info. A few hours later, the agent from my MC called to tell me he had a family emergency and would contact me later. He did, but it was an inconvenient time for me, and I asked him to call me back on Wed or Thursday, last week, and he still has not, 4 days later. I don’t have the information from Ann, yet, either.

If there is no activity regarding purchase of my rental within 3 months, I want to be able to rent that house, using that same MC, but don’t trust that sales agent.
I trust Ann, but don’t know if, while it’s listed for sale with her, if I can rent it through my present MC without some backlash from them.

I prefer to continue seeing houses with Ann: we’re sort of friends, I think she knows what she’s doing, she rescued the purchase years ago, and I’m confident she will protect me as far as she can, as long as I remember HER loyalties to her broker, to herself, to the seller, and then to me.

I think my questions are:
How can I best protect myself?
How, and with whom, do I structure a sales/escape clause in a sales listing contract so that I can rent the rental if it goes to long unsold? What should it include?
What to do?
List the rental to sell with my present property management co?
Or
List the rental to sell with Ann?
Can I realistically list the rental to sell with Ann, and in 2-3 months, plan to rent it w/my MC if there is no activity re selling?
Bite the bullet and just plan on a 6 month sales contract and if no activity, to rent it after that?
Do houses that are rented/inhabited sell easily?

I want to be fair with Ann, she’s given me a lot of time, (Which is her job, as a friend says)
But I need to protect myself, financially.
What would you do?
All comments, suggestions, welcome, and thanks for reading this. Help me out, please!

What else should I be asking?
thanks
ofgift