2. Rogue was correct when he referred to Players handbook #1 saying on page 295, 2nd column, under the section titled "healing a dying character" it says: "When you subject to a healing effect that requires you to spend a healing surge and you have none left, you are restored to 1 hit point, if you were dying."
Point 2 is technically correct but not relevant to your situation.
A dying character that receives healing of any kind that requires them to spend a surge but who does not have a surge to spend regains 1 hp regardless.
But that's not the issue here.
In order for Point 2 to apply, the ranger needs to have received "healing". p293 of the PHB (4th paragraph) states : "Powers, abilities and actions that restore hit points are known as
healing" (sic).
A heal check is only a "Powers, abilities and actions that restore hit points" if it results in the successful use of second wind. Otherwise it does not restore hit points.
To put it a different way, the second wind is the "trigger" for Point 2, not the heal check.
In your case, the ranger had no second wind to spend, therefore didn't receive healing, and point 2 is therefore irrelevant.
So the heal check does nothing, and the ranger stays at -X.
On that basis, it's not really necessary to deal with point 3, but I'll touch on it because I think you might be misunderstanding its application:
3. BUT...In Players Handbook #1 on page 295, 2nd column, under the section "healing the dying" (in other words the same section Rogue was referring to) in the second sentence it says "If someone has stablized you using the heal skill but you receive no healing, you regain hit points after an extended rest."
So you were both wrong? So this last part has me thinking that michael and matt need a full extended rest to get hp back
Point 3 refers to stabilising.
Healing is not stabilising. They are different mechanical concepts. As far as I am aware, the only way to stablise a dying character is through the "stabilise the dying" application of the heal skill. Any healing at all returns the character to positive hitpoints, and thus consciousness.
Point 3 is therefore a very corner case and doesn't apply to your situation. The rogue didn't stabilise the ranger.
If the rogue stabilised the ranger with heal the next round, then point 3 becomes relevant and your interpretation of the rules is correct.