Hopefully they would answer YES, and you can proceed to find out whether you can have them owner finance you (if it is free and clear...or ALMOST free and clear...)

We'd like to sell it and use the proceeds to buy a new primary residence and then either convert our existing primary residence to a rental or sell it and buy some different rental units.

If you are 5th in line, you might want to also start looking for some other properties in the meantime.If you  have only a tax certificate, it is sometimes hard to get property insurance.

Proceed with caution.

Master insurance policy issues can be daunting as well.Seems to me that it would be easier to construct a duplex.  

So I've complicated your decision a bit here on what you should use the cash out net proceeds for....

Make sure though that they are licensed and insured to do snow plowing and not just a "chuck in the truck" because there are a lot of those offering plowing services.

I am an Insurance agent by day and real estate investor by night and weekend. 

This will not be considered toward sale price if tenant wants to execute the option.Lease : $2,000 - Fair market rent.Tax and Insurance -- Landlord responsibility.Utilities and Maintenance(Lawn) - Tenant responsibility.I appreciate your time and advice.

I could use a little advice from some of you experienced folks on how to proceed.