A delead contractor needs to see an inspection report to have an idea. otherwise they are just pulling stuff out of thin air.

To add to the damage, this home is located in a subdivision with a $95 HOA fee.

You will likely have an easier time collecting on any damages from them than a random tenant.  

I found it on MLS, negotiated a decent price, then renegotiated after the inspection found a significant water leak and related damage.

So I think you will have to figure out what the real damages are from the lease extension and if it is worth the time.

There is no structural damage, no flooding, etc and the appraiser stated the home was in good condition.

water lines in the ground last 60 to 100 years and do hardly any damage when they break.

Everyone likes something different so I think even one of the air adjustable beds wouldn't make people happy because it takes a while to figure out your "sleep number" and for someone staying one or two nights they probably wouldn't have it dialed in.To answer your question, I don't think there would be a return on your investment for the Craftmatic.

Avoid the biggies like foundations, termite damage (unless it's easy to access and fix), mold / lead paint / asbestos remediation, full kitchen/bath remodels, etc. 

Thanks  Also remember that these insurance companies cover damage by guests, but not typically issues related to contractors, service providers and vendors.