Fix the problem and make them pay for it.   

Hot tubs pay for themselves.  

The agreement is that your tenant will pay for any damages they caused.

But I need a portal where I can do the following -Customize the tenant application  ( Cozy does not  allow me to customize)- Have tenant Upload Pay stubs, DL, etc. 

I am finally at my two year mark not being W2 so if I can skip past DSCR loans and the such that would be much preferred as I dont want to pay the fees if I don't have to as I am trying to get some money I put into each unit to renovate back out of it. 

I would keep the deposit unless I am able to rebook the dates and then I would only make her pay the difference for any unbooked nights. 

With regards to your example about plaster vs. drywall most insurance policies no longer will pay for the plaster whether you have a public adjuster or not. 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Section 8: Rents are too high for the program and cash paying tenants are better overall.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsSection 8: Rents are usually too high for the program.Class C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Then she still only makes 2% extra for taking the risk of you not paying versus a bank.

You can too, without being a wholesaler or an agent.You can walk into a mall to a jewelry store and buy gold, which is simple, but you pay a huge markup.