You wish payments on April 1 and October 1. Thereafter, as each bond matures, you use the principal to purchase another 5 year bond. If, at the end of 1 year, interest rate have dropped, you still have a portfolio already invested in longer term bonds at a higher rate. If interest rates have risen, your returned principal will be invested at a higher rate. Interest rates will depend upon how much risk you are willing to take.
Government bonds are essentially risk free as well as free of state and local taxes.
Rates will be higher for corporate bonds, but so will be the risk. The lower the bond rating the higher the risk. Due to interest rate fluctuations all bonds are subject to substantial gain or loss if sold before maturity. If you hold to maturity you will get back your original principal but in the event of inflation it may be worth less. Your broker or financial planner can set up a ladder for you.