Definitely a Goodwill thrift store look that I'm not loving.

I've brought this issue up with my PMs and they tell me that even if the tenants conduct contributed to the problem, if you want to run higher end rentals with desirable long-term tenants it's advisable to let the charge fall back on the landlord.We just look at it as part of creating goodwill with good tenants, which I've concluded myself is long-term the best approach.

If he does not make it good then at that point you have to figure out if you are going to simply use the 150 thousand loss as a hard lesson learned or whether you will permanently Destroy all future possibilities of Goodwill between you and your brother in law.

Are PM guarantees typically explicitly written into the management agreement (or the additional document referenced somewhere in the management agreement) or are they typically offered as a business policy that the business will offer on their goodwill but not written into the contract with homeowners? 

Anyone good will not be cheap.

I think it might build some goodwill.

The robber baron's cruelty may sometimes sleep, his cupidity may at some point be satiated; but those who torment us for our own good will torment us without end for they do so with the approval of their own conscience.

I would rather generate/recover goodwill with the tenant than an expectation if something goes wrong they'll be compensated.  

Contractors (if they are good) will do any job faster and better than I can.

Contractors (if they are good) will do any job faster and better than I can.