If Landlord has filed an eviction due to Tenant’s Default or other breach, including breaching for non-payment of Rent, regardless of the outcome or disposition by the court, Tenant agrees, upon request, that the court shall make a determination who the prevailing party is in any eviction and whether any attorneys' fees and court costs sought by any party are reasonable.

I do have additional coverage for the sewer since I knew it may have issues before I bought the property. 

Additionally, do you have any other ideas or strategies that might help achieve his goals without incurring a tax liability?

The only additional thing that needs to happen is make sure appraiser makes note of why the value increase in as is vs previous purchase price.

I know this is a very old thread but if anyone comes across it I wanted to add some additional thoughts that might be helpful.

Very interested in the Cleveland/Ohio market in addition to a few other cross-border cities closer to Toronto. 

If you feel the agent mislead you or rushed you to sign off, you may be able to file a complaint.

Experience depends on who you deal with - the cleaner the loan file and more organized your paperwork the smoother the process with any private lender.

- The management company keeps track of finances and offers reports to the owners that are prepared for their accountants for tax filing.- The owner has full ownership and control of the property and can make all decisions such as when to sell, or may decide to operate the property according to their own wishes even if those wishes are against the recommendations of the property management company.

If their guest falls down the stairs and breaks a leg, you would be covered under the tenant's policy and wouldn't need to file with our insurer.