Unless you were planning to do them anyways. 

Would you lend your own money to someone that is planning to buy an investment property, but has no experience managing one?

But the same argument people use for self managing, (nobody will care as much about your property as you.) is definitely true of your accounting. 

We plan to sell and use the $500k exception to the capital gains taxes because we lived there for two years. 

**Contingency Planning:** What is your strategy if you need to repossess the property?

A cost segregation study is a strategic tax planning tool that separates the assets that have a shorter useful life and can be depreciated over 5, 7 and 15 years from the residential rental property or nonresidential real property that are depreciated over 27.5 and 39 years, respectively.

Its a fee for tax planning and financial advise. 

(I'm an estate planning lawyer - not an insurance agent).That being said --- you really need to sit down and understand your goals before you get advice on what vehicles you want.Insurance people will tell you insurancelawyers will tell you to set up a ton of LLCs and trustsNone of these are correct if your goals don't align. 

> If you self-manage, has that been more difficult than you originally planned?

A few helpful clarifying questions, hopefully help get your wheels turning as well, would be:What are you planning on doing with the property and what is your exit plan?