There may be another option to your current choice of cutting the rent or cutting the renter loose...If the renter has been able to pay $2600/m for the last three years, they may have some other financial accomplishments to be proud of.  

Success is a process, failure is a choice

Success is a process, failure is a choice

Depending on your reinvestment opportunities (return rate) and your opportunity/hurdle costs of other capital sources, an extra $2700 in pocket today, might be worth paying an additional 50K for the asset.One might also convince themselves it is a better choice to pay 2.5 times more in the way of interest (252K) in exchange for $1100/yr in pocket and the security of a fixed payment for half a century ... though, personally, the inflexibility of being corralled that long could never be worth it.  

Good choice, I think.I guess I'm going through some kind of mid life crises.  

You have several choices.  

Your choice, BUT a 10yr roof is not 'in poor condition' unless A) it  was installed 11yrs ago B) an inspector says so in writing. 

Success is a process, failure is a choice

Mortgage payments that are due cause landlords to make poor screening choices!

I finished my PG in 'Strategic Management' from Toronto in 2012 and worked as a financial analyst for few months.