Why is it so hard to comply with the securities regulations?
Simply because it is a "Gotcha."
A Gotcha is a system of rules that is virtually impossible to comply with so that the regulators can decide who to prosecute and then run in on that person and yell "Gotcha!"
Now you might think that this gives the regulators too much power, but I believe that they proceed in good faith and that this is a useful system. They do not have time to hit every violation and so they must have discretion.
In fact, some rules are deliberately left vague because the bad boys continually try to design around them and game the system. In fact, I suspect that felons spend much of their free time in jail working on such solutions.
If the rule is vague, the regulators can thwart any such wrong intent easily.
Thus, you will find rules that outline what you can do and then end with the warning that says in effect, any attempt to get around the rule, even if technically in compliance, will be a violation.
I will advise you that any attempt to comply with the rules must start with a pure heart, an intention to do right by the investors, and then worry about technical compliance.