what do you think the property is worth today?

For clarification I actually intend to live in this property for the majority of the year. 

When a property is sold it triggers an inspection to get the property up to code.

So with all that, I'm thinking to open booking now for next summer with a 7 day minimum, see how it books out, and by late winter/spring I can reduce it to a 3 day min to fill any remaining weekends, and then work on filling mid-week vacancies as summer approaches.We were leaning towards Fri-Fri, but Michael I like your suggestion about the Mon-Mon option, which could be nice because renters would have the weekend to travel and then begin their stay on a Monday, then they would end their stay on an upnote with a long weekend...But with either Fri-Fri or Mon-Mon renters would probably need to take 6 days off work...Sunday-Sunday might actually be better because renters would only need 5 days off.  

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.  

So if your property is not placed in service until 2025, then your bonus will be under 2025 rules, i.e. 40%.

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

I'm unsure what the right path is, but I've been reading about investing in owner-occupied, multi-family properties.

This is actually biased media with an objective (including Tampa Bay Times).