@Matt GeertsWe added the ability for the optionee to petition to annul the option (BTW: it's not automatic it would happen) because we were concerned about appearing predatory in the scenario such as you raised earlier (i.e. where the Tenant gets evicted).   

Which, incidentally, could hurt your ability to earn enough money to pay it back...

I would always RUN, RUN, RUN from anyone claiming the ability to get you a private,  low-interest rate loan and are asking for upfront fees.

If so, when you went through the mortgage qualification process, did the 50k loan hinder your ability to get the new mortgage? 

Really if you can never imagine running a weed whacker or fixing a loose deck rail or mowing a lawn, then the condo may fit your rental management abilities.

At SXSW I saw one of their people and they said they will have the ability to get bids on jobs like cleaning, painting and such soon - I assume this is how they make money. “ Ben TravisPros: they are new and offer free operations for landlords and tenants Cons: new company, not mentioned on BP much Cost: “We get paid by service providers - like insurance companies, plumbing companies, screening companies, A/C and heating, moving companies..... oh you get the idea.

It's also much easier to find partners, joint ventures, and lenders using creative financing if your deal analysis abilities are solid.

The key is where you end up at the end of your 1031 in such a way that your cashflow or ability to continue pursuing your passion is maintained.  

At SXSW I saw one of their people and they said they will have the ability to get bids on jobs like cleaning, painting and such soon - I assume this is how they make money. “ Ben TravisPros: they are new and offer free operations for landlords and tenants Cons: new company, not mentioned on BP much Cost: “We get paid by service providers - like insurance companies, plumbing companies, screening companies, A/C and heating, moving companies..... oh you get the idea.

I think it would depend highly on the town itself as to its ability to draw visitors from other places either as tourists or for business.For your Airbnb in Toronto, did you use a management company or do it yourself?