The stays at your property are mid-term, but for repeat business, you want to cultivate long-term relationships.It sounds like you are well on your way to doing that.

The type of loan on your current property is largely irrelevant. 

My question is - Bracebridge is experiencing issues for long term rentals for people looking to rent a 2 or 3 bedroom unit, and these are very scarce as prices to own escalate and property management for long term rentals is scarce also.

My advice is to buy good properties in good locations even if you have to forgo cash flow.  

I know some regular conventional investment property loan programs have certain rules about this but does Fannie Mae?

We use it for managing our portfolio of SFRs and small multi's and it handles everything accounting wise for the properties so there's no need for quickbooks.You can also run your property management business expenses through Buildium or use Quickbooks if that's easier. 

- Should I purchase the property through an LLC for potential tax benefits?

Property taxes while you hold the property. 3.

Mixed-use zoning has been a goldmine for many of my clients, particularly those who started with owner-occupied properties and later transitioned them to full commercial use. 

As a teenager, I managed properties that I owned a percentage of.