Managing options in quicken

I feel your pain.  Options do work in Quicken although it's not perfect.  I have been doing lots of them for years (although I may stop tracking investment transaction details in quicken in the near future).

1).  Expiration/assignment have to be handled as CvrShrt or Sold transactions.  Agree that Add/Remove is probably more appropriate and some brokers (e.g. TDA) will download then as Add/Remove.  Others (e.g. Schwab) download them as Expire/Assign but Quicken will convert these to Sold/CvrShrt.
2).  When options expire I suggest you hide the security (security list).
3).  Don't even begin to think the Capital Gains report is correct.
4).  Not all brokers not all follow the OCC symbol convention (e.g. TDA) so in these cases quotes will not download for securities created via the downloaded transactions.

Levoy H said:

Well, that confirms what I was afraid I was seeing, so thanks for that.  The short positions seem to be the most problematic.  I have accounts at TDA and ETrade.  When a long position is closed they download a "sell" transaction, which at least keeps the number of contracts/shares correct (ie, zero).  However, they also use a sell to close a short and that just doubles the number of shares in the short column.  I've been changing those to CvrShrt to zero those out.  Fortunately these are all in tax-deferred accounts (for now) so I don't care about cap gains.  

I can see your point about not tracking this stuff in Q - it's a major PITA.  

And the problem w/ the download may or may not be w/ Quicken.  You need to look at the OFX log file to determine what the broker actually sends to Quicken.  For example Schwab sends the correct transactions (Expire/Assignment) into Quicken and since Quicken doesn't have expire/assignment transactions it translates them (not always correctly) into CvrShrt or Sold.  TDA sends through Add/Remove transactions instead of correctly sending through the Expire/Assign transactions and Quicken does not translate these.

One item not mentioned here...  Transaction type, "Add /
Shares Added"...This happens when Fidelity reports a transaction
incorrectly (I'm inclined to think it happens when I've closed an option Spread
[Buy-to-Close & Sell-to-Close].  I forget which transaction
"type" generates this (incorrectly), but I've resigned myself to "Covered
Short" at ZERO transaction Cost and the incorrectly ADDED shares are
eliminated, and the "remaining balance" is then correctly shown. 
Not a major aggravation, but solves the problem.  I wish Quicken would
"adjust" its software to somehow perhaps have a "pop-up"
that asks the user to "select" the correct transaction
"type" (i.e., Buy, Sell, Cover Short, etc.) for transactions that have
been downloaded but NOT yet ADDED to the account's Transaction log. I’ve
always added transactions MANUALLY, so I do this without FULL mental awareness
typically.   I expect that 98% of all transactions do NOT
need this scrutiny, so this pop-up should have a "fast" or
"nearly automatic" method of dismissing/accepting it without added
effort from the user (other than perhaps a quick mouse click or ENTER key). And
if the user wants to accept it, the default entry would be "Accept this
transaction" in a drop down box... but of course the drop-down box would
also have the other "possible types" as available choices. 
And amazingly, I can't remember specifics about these issues since I don't
currently have a downloaded "incorrect" transaction to accept (...
but, as I should add, I've ONLY been a Quicken user since the early 90's, so a
few thousand more transactions and I should be able to remember)... Kind of like losing your
car keys, ... I JUST HAD THEM 15 SECOND AGO...

My question relates to whether I should enter the option position of a single stock with different expirations or different strike values as a NEW stock or accept the common default that option positions of single stocks with different expiration dates or strikes are the same stock (option).