Simply looking at financials is frivolous and dangerous and such recommendations threaten the longevity of his wealth. 

Or should I attempt to evict him or something along those lines before the time comes?

Fill it out correctly.Do not waste your time or effort to attempt to evict (N4) as it will fail and you will lose your application fee.For non payment of rent the board will rule in your favour every time....make sure you ask that the tenant reimburse your application fee.

I’ve been attempting to deal with this for the past several years and can’t seem to develop a strategy that I’m confident with.

@Ernesto Correa is this an attempt to get a home office tax benefit?

Im looking for something really simply and dummy proof.

Attempt to contact your current tenant.

@Ryan Gill Unfortunately the bank will not likely let you simply assign the contract and change the buyer, so you may have to double close like Ned suggested. 

We in NO way want to under pay any good work, but this is simply taking advantage.

For this the simply tack on the price of a one-year renewable term policy.