As far as SingleKey actually paying out on claims for tenant non-payment up to 12 months, property damages up to $10k reimbursed, covering 30 days of vacant property losses and helping out with tenant evictions up to $2k (as advertised), curious if anyone on here can attest to SingleKey actually paying out on these claims successfully.

Then things went south...I decided to gut the rest of the basement since it got water damaged from the foundation issue.

@Rosette PooleRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Quote from @Alex Tang: One of my rentals was heavily damaged by a fire after Thanksgiving. 

It's all in how conservative you are in your approach to underwriting your deals.Even when a Seller says they've improved the property, the tenants are still tenants and do damage to brand new improved units. 

In addition you can use it to collect initial security deposits or to bill the tenant for addition items such as billed back utilities, damages, etc.

Ask an attorney for the cost breakdown, factor in holding costs, assume they'll do more damage on the way out and then ask for a bit more for the headache.But again, especially with no experience with evictions and it sounding like a mess, I would be very tempted to just walk if the tenant is not going to cooperate. 

We're considering doing something like Dave's cookies via Amazon but that's only semi-fresh baked and subject to shipping damage. 

Does the contract include a monetary damages provision?

If you tell the constable that you are concerned about damage, they may talk to him about leaving responsibly.If you are concerned about violence, have a means of defending yourself and let him know it.