The tenant wants to stay another 2 years.My other adult properties have often had long-term tenants.

I use Stessa to self manage 8 properties.

Insurance right now is wild, so I'd get a solid broker on your team - I'd be happy to share my contact if that would help.Also, aren't most of the existing insurances shared on the OMs for the properties? 

Mind you, we are mortgage free too, but that is really a function of the buy/price.

Are they doing everything possible to expose properties to the broadest possible market?

So your capital gain when you sell this property will be calculate against your tax basis and not against your mortgage as many investors expect.

Is this property in TN?

No issues on property, except a faulty leaky toilet that was fixed same day as tenant posted maintenance issue.

I know a common practice (at least for syndications), is to create a separate LLC for the property and then raise capital once the deal is already under contract.

If you decide to sell and find an investment property with a greater cash flow potential.A 1031 exchange would allow you to indefinitely all of the tax and use it to your advantage to reinvest into larger nicer property/properties.