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

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.

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.

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

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

Obviously, I don't want my properties making people sick.

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. 

What are standard terms and conditions when raising capital from investors for a real estate investment?  - Who carries the personal guarantee on the debt?- What is the standard GP / LP split?- Are deals that are fina...

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

Don't think you need to buy the first property that comes your way (I did that initially...actually just sold it at a break-even after all expenses).