Spirit/intent vs strict reading. Your scenario has enough differences from what the DPEs normally see that it will raise some questions as described.
Multiple days - should not be an issue. After all, you can log it on one line or log it on 3 or more lines depending on how you usually like to log.
Giving friends rides - this is a tricky one. It's my opinion that the trip in its entirety meets the spirit and intent of the regulations, however, it probably wouldn't pass muster with a DPE*. And that's simply because of the "a XC flight" language. While breaking the trip up into multiple days can still be called one flight, it's harder to argue that a "solo XC flight" where you stop for local flights with passengers can still be considered the same flight.
* Reason 182 why I am not a DPE. I think this would be a great trip to use to meet the intent of the requirement, but I just can't see it passing an "audit".
There are certainly other ways to make the logged flight acceptable.
I also see a problem with the rides. The regulatory language is, "One cross-country flight .."
The multi-day thing as constituting "one cross country flight" is pretty well established. The old orphaned Part 61 FAQ said, "The 'original point of departure' for the purpose of a cross country does not change with a new day or delay." The same concept later found its way into a 2009 Chief Counsel opinion letter:
“There is nothing in § 61.1(b)(3)(ii) or previous FAA interpretations dictating how separate flights must be logged. Accordingly, the pilot may choose what is considered a discreet flight and what is merely a segment of a flight, and then log that time appropriately when the flight is conducted. Section 61.1(b)(3)(ii) requires that the flight include a landing at a point other than the point of departure.”
So, for example, my long solo commercial cross country covered three days (if I had been thinking about the requirement, it would only have been one[*]).
But, especially considering the
solo requirement, it's harder to say that
Day 1: AAA to BBB solo;
Day 2: BBB to BBB with others on board;
Day 3: BBB to CCC solo;
is "one" cross country flight while solo. Even if the rides don't break up the cross country, the people on board breaks up the solo nature of it.
[*]
but it's so much better when you're already doing a flight that meets, or almost meets the requirements
That was mine. It was a business trip.