Ahh...the classic question is now coming up. I have spoken to numerous attorneys about this and IMO it is really a definition of degree. The classical case is SEC vs. Howey where the definition is clearly defined. Here is a decent piece of literature I found doing a quick Google search:
Clear As Mud?
If you Google "Howey and Security" or some such you can read through reams of information and fall asleep quickly.
I saw an opinion recently from a well-known CCIM/Securities attorney that has written several popular books that claimed loans are likely securities. Here is part of that opinion:
//Quote Trowbridge
Sometimes an investor who is looking for one other person to provide debt for a transaction, perhaps in the form of a hard money loan, is not working with a security. In a hard money loan, with a one-on-one relation between the borrower and lender, it is likely that no common enterprise exists. If the borrower does not pay, the lender forecloses, as the relationship is more adversarial than a common enterprise. However, some attorneys take the position that if there are multiple beneficiaries or if the note calls for equity participation, debt may likely considered to be a security.
In a strict equity raise, the issue of whether a security exists is likely dependent on the control of the project by one or more persons, as in a manager-managed LLC. When all decisions are made unanimously, as in many member-managed LLCs, it is possible that it may not be a security.
//End Trowbridge Quote
I don't know all of the circumstances in the questions above, but the passage from Trowbridge points to the common enterprise part of the securities definition. I think a helpful question to ask is whether or not the relationship would put folks on the same side of the table in the event something goes south (a common enterprise) or if the relationship would be adversarial.
I have a hard time believing that individual loans combined to capitalize independent pieces of a transaction could be considered worthy of a reg. D exemption. However, if you start to pool more loans to capitalize your transaction, put together marketing decks for new investors, or pool many investment dollars into "one loan" that to me is more security-like and I would want the exemption.
Really it all boils down to risk tolerance at the end of the day. If the deal goes south I want as much protection as possible. PPMs are set up to protect the promoters...not the investors. If you can pay the loans back out of your own equity and use the loans to keep less of your capital in a deal you really could just pay the loan back presumably. If you can't then I would want more protection.
Clear as mud...eh?