how did it work out for you?

Your job is to educate them on market conditions and long as you don't lie about your professional opinion everything should work out fine.

I’m not gonna break lease but if we can work out any way out of it best.”

So be smart, do you best and it will all work out as long as you don't quit.  

Rent is due when it is due, your priority is collecting rent on time not collecting late fees.This tenant sounds like he is not going to work out if he "expects" to pay rent when he chooses.

Originally posted by @Joe Villeneuve:You need a partner.I have a couple people with some expendable cash that would maybe be interested in making some money with me but they are also incredibly busy and work out of town (both on oil rigs), so lining up our times are incredibly difficult. 

Most annual renters here are restaurant workers or people tied to tourism or retirees.In the 3 years that we have known this gentleman he has only had one renter that lasted for 4 month before she told him that she could not afford the rent.Gentleman does not need the money, but finally figured he still could make some money off of his property.So he approached me and asked if we would manage vacation rentals in his unit for him.I told him I was not interested in managing for him but if he was interested in renting to me and let me sub lease to do Vacation Rentals my self we might have a deal.He said he would rent 5 units out of 7 since he wants one for himself an 1 unit for family members when they visit.So I said give me a price for all 5 units to lease.He came back at $2200 a month if I rented all 5 units.I told him that would work.I then asked, how about if I give you one year rent upfront on 5 units, We finally agreed on $100,000 up front for annual lease of 5 units.That works out to $1667 a month per unit , what's that work out to?

Admittedly, it doesn't generally work out that nicely but it's not unusual for someone to buy and rehab at 80%...so 5% out of pocket. 

(Did the carpet survive, are the appliances still acceptable move-in condition, misc wear and tear)I start most tenant with a year lease and if they work out the new walls are 2-4 years usually at a time.

It may work out for you!