I really don’t mind that fee, but $150 renewal bothers me a little since it’s an email with the terms I set. 

Ideally it has a separate entrance and will not bother other tenants.

@Cody Kayser, I actually AM a Realtor, but I still rarely even bother with listed properties.

Why bother asks the contributor, looking to the sky...

Don't bother with removing it until you're ready to replace the roof or you'll just introduce another problem.Do a good search for "how to cap unused chimney" and you'll find a lot of resources.

Ask him to credit you a portion of the lease payments and when he asks why tell him you're saving him all the hassles, and its your incentive to never bother him about the property (which if he's heading into retirement he doesn't even want to know he still has a property.. just wants a steady check automatically deposited to his account) Offer an all cash option that is not obscenely low, but if he were to go for it, that you could find a partner (someone with the extra capital) to make the deal still happen.

Given the small amount of the debt and the unlikelihood of a successful recovery, it is not worthwhile.If you want to enforce the debt in NY, you will need to research their laws, but it will likely be unenforceable or too expensive to bother with.Most landlords do exactly what it is your doing.

They add a pop of colour on a sofa, but if you have a blanket on it or the sofa already has a pattern, don't bother. 

If handled right away, the amount is probably not large enough to bother suing them over but that would also be an option.

I don't bother with small claims.