If both Realtors were members of a local association there may be a path to arbitration that would not necessarily have to involve legal council.

You may want to seek legal council to determine a similar model, which from my understanding is not impacting the due on sale clause. 

Try looking at the townships north and west of Duluth. there's opportunities there for STR's without the Duluth city council taking the hotel money to shut you down. 

Do any of you know what the status of vacation rentals with the city council currently is in JT and where it's likely to go?

Although you may be able to get great information from the local jurisdiction and its written development plans and ordinances, it will be the will of the people - either directly in neighborhood town hall meetings focused on such issues - or indirectly through their elected or appointed officials involved in the (again, political) process (planning commission and county commission or city council meeting for the purpose of considering such proposals) of coming to a decision on your proposal for a use different than what already exists.This is not a bad thing - the same emotions that drive neighborhood positions also drive care of existing properties - and thus, their and your land values.A land-use practitioner may be a great ally throughout this process - ask around among others who have navigated these waters and interview the most likely of their suggestions to find one sympathetic to your cause and not antagonistic to the political powers-that-be.  

--City Council approves plans aimed at halting South LA gentrificationhttps://www.scpr.org/news/2017/11/22/78027/new-dev...

Council Bluffs in Iowa?

I would talk to people that have been in that area a long time and are community involved like the Chamber of Commerce, City building inspectors, real estate Agents,  BBB people, City Planning and Zoning people and City Council people or City-involved business people.

Does you city council/county offer a flat rate for multi-dwelling apartments?

Ask the redevelopment council member if it would be ok to stop by from time to time.