If the tenants don't care for the pool properly, it could cost you thousands to fix.

You will need an attorney to properly structure the partnership and you will make sure you do it correctly.

I think your biggest issue with any "work-arounds" is going to be your legal liability and holding the proper insurance in case something goes wrong, which I'm going to assume you'd need to be properly licensed in order to be properly covered by insurance.

Hardly anyone can prep properly, mask or dropcloth properly, cut in around trim and windows, get even coverage, etc. 

If the proper reports and documentation are not completed, you run the risk of failing an IRS audit and the cost segregation not being honored.

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.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 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Market timing, properly acquired property, personal capital available How did you find this deal and how did you negotiate it?

Once you've identified what's important and what ratios to look for to evaluate a property, all future deals should be weighted against those "good" ratios/numbers - and periodically adjust to suit your goals.

Let me know if you plan to make it so I can let the owner know and he can make sure they are properly prepared.

Still up to me to properly utilize it and get the deals contracted.