The issuing of bonds is an issue not talked of for private limited companies as it is not a common source of finance.
For a PLC, it is common because these debentures are tradeable, and have a value, especially when they are Convertible loan stock (ie becoming share capital at a predetermined time)
The only two general rules pertaining to issuing debentures are
1. does the memorandum and articles allow these as instruments, or do you need to change them to have them allowed?
2. who are you seeking to take up the issue of debentures (ie even a private limited company if seeking outsiders to subscribe, must produce a prospectus). However if I offered to invest 20k, and you offered me debentures and I was happy with it, then there is no need to issue me witha prospectus, as I am already known to you.
I accept the above is a bit simplistic, but its basically correct.
However, here is the point.........
Debentures usually carry a coupon value (interest %), that is generally payable every 6 months, so if I injected my mythical 20k to your company, I would be seek a rate better than I could get with say Santander.... So for ease of maths, you issue me with 5% debenture stock. ie I get 5% of 20k over the life of the debenture, generally 500 pounds every six months, but for how long a determinate amount of time??????
You could make it a 10 yr debenture, so for next ten years I get £1000 each year, and at year ten I get my 20k back, however, what if interest rates rises, and Santander offers 6%. I'd be stuck with your stock, and as a private company, couldn't offload it, so basicaly am I willing to gamble that your rate is higher than Santander for next 10 yrs. Nope, as duncan Bannatyne would say "I'm Out"
Assuming I am still in and if it were a two year debenture which I have seen on many occasions, why would I invest the money for little above Santanders return, and then after two years, be repaid and told to go away. I'd love to see you get an overdraft at 5%. So if you offered me 10%, I might do it, but you'd get an overdraft cheaper, however as the banks wont lend, you'd be stuck with me.
Complicated? Yes and no.. complication is only caused by greed. For me I'd not want to lend you cheap money and then be repaid. Either my debenture is convertible at some point to share capital, so I'd have a stake in your company, or else I'd ask for preference shares. However for you, debentures are cheaper as they get tax relief unlike paying 5% or 10% dividend on shares.
Again with debentures, I'm more protected in case you go into liquidation than a preference share holder.
Bottom line:::::
1. Check your Memo & Articles
2. Review your forecasts to see if Shares or Debentures are your best course
3. Negotiate with potential investor as to the return they will get & their protection.