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I want to make sure how to use perfect tenses (past and present) with have for possession:
Suppose I bought a car a few month ago and I sold it today. Can I say:
I have had a red car for a few month, but I sold it today.
Now, suppose I bought a car many years ago and sold it a few years ago. Can I say:
When I had had a red car, I went out every weekend.
Am I saying it right?
Now, suppose I bought a car many years ago and sold it a few years ago. Can I say:
"When I had had a red car, I went out every weekend."
You only need one "had". With that fixed, this would be correct.
Suppose I bought a car a few month(s) ago and I sold it today. Can I say:
"I have had a red car for a few month(s), but I sold it today."
If the buyer asked you before the sale "how long have you had this car?" then you would answer "I've had it for a few months." But once the sale is over, you don't have it anymore. So if people asked "How long did you have that car" you would say "I had it for a few months."
Yet you are relating a contrast about something that happened today. And today is a span of time where the car was in your possession for some of the time, and not for the rest. So you can get away with saying "I've had a red car for a few months, but I sold it today." While you're in the state of transition, you can still speak about 'having' as part of that.
With just this sentence, much more clear-cut would be to go ahead and just say "I had a red car for a few months, but I sold it today." But there may be reasons in context that you'd want to use present perfect (emphasis on the result).
See this Q&A for more on the difference between "have had" and "had":
The difference between the present perfect and past perfect tenses is that the present perfect tense relates to something "past to the present" while the past perfect tense relates to something "past to the past". E.g. the ownership of the car has been going on until now (present perfect):
I have had a red car for a few months, but I sold it today.
The ownership of the car went on until yesterday (past perfect):
Yesterday I sold my red car, because I had had it for several months.
So the past perfect had had should only be used when you're describing a certain point of time in the past and the events before that certain point of time.
About your use of had had: if you went out every weekend when you had the car, the other had is one too many:
When I had a red car, I went out every weekend.
This is simple past tense, describing the past.
However, if you waited for two months after getting the car before you went out every weekend, then:
When I had had a red car for two months, I went out every weekend.
This is past perfect tense describing the two months leading up to the point in time in the past when you went out every weekend.
