1. Debt design
Aswath Damodaran

2. The key idea Debt that behaves like equity
If you can tie the cash flows on your debt closely to the cash flows from operations (on your assets), you can borrow more money at lower rates.
That will lower your cost of debt and cost of capital.

3. Intuitive Debt Design
Start with the typical project for your firm. If it is multiple businesses, each business may have a different project type.
Think about a security that will meet the debt test (finite maturity, contractual payments, consequences from failure to pay) with the payments tied to the typical project’s cash flows.

4. Let’s try Walmart Typical project The perfect debt
A new store, with a life of perhaps years.
Cash flows are in whatever currency applies for the location of the store
Mildly cyclical (because it is a discount retailer)
Very little pricing power
Mature company
The perfect debt
Long term (12-15 years)
Currency matched to where Walmart is opening its stores
Fixed rate (payments)
No conversion options or equity tweaks

5. To try to get more specific answers, you can look at your company’s history
To do this assessment, your company needs to have a long history. Start with the following data:
Market capitalization at the end of each year
Total Debt outstanding at the end of each year (You would like this to include PV of leases each year but that may be asking too much)
Operating income each year.
Suggestion: Use the Bloomberg terminal to good effect. If you find your company, type FA and the pick the Enterprise value tab, you should get all of this data for as many years as you want.
Aside: Your life will be a lot easier if you have a calendar year end.

6. And look at the relationship with macro variables
You could look at macro or external drivers of your company’s value. For instance, here are four standard macro variables:
Long term interest rates
Real Economic growth
Inflation
Currency
Getting this data for the US is easy. (FRED) It should be available for other countries, but it may require more work.
You can also add other macro variables that may impact your company (Defense budget for a defense contractor, Oil prices for an oil company etc.)