If they know you, have spoken to you many times, and you have always been friendly with them, just explain your points, that there is no legal reason to deny your plans, and ask them what you can do to help get it approved.

To help avoid a lot of these issues I would think about buying a "Modular" or use a "Tiny Home" vendor who offer these in many states.

@Marc Shin, Soundproofing is definitely something worth tackling for a short-term rental—it’ll keep your guests happy and help you avoid complaints.

Now, I’m rebuilding my portfolio while continuing to help others buy and sell homes.

We have an amazing realtor who helped us find the property and helped us run numbers on possible ARV, @KiKi Wood. 

And will you be utilizing property management firms to help out? 

I have helped Canadians purchase real estate here in the past.

I also have lots of connections all over the nation to help.

My vision is to keep it a while (it’s paid off) and use the cashflow to help with my kids college.  

I want to know if there is anything I can do right now that will help me in becoming a realtor in the future.