Q1 - I acquired stock over multiple years/acquisitions, do I report these as separate transactions - e.g. 3 different purchase dates, but same sale date - do I record as 3 transactions or can I record as one transaction with total basis and total sale using the first acquisition date as date for all 3?
if the holding period for all is either long-term or short-term, I would report all as 1 transaction. the issue you would have if each purchase/sale was reported separately is determining your tax basis of each acquisition. however, separate reporting would be required if some were long-term and some were short-term.
Q2 - There is an option in TT to add expenses to the transaction. May I legally include some or all of the legal and valuation expenses personally incurred as part of process to determine the sales price and execute the sale? If not part of the sale, may I include these as unreimbursed business expenses? Any nuance I should beware of?
since you say you sold the stock, the expenses you mention would be added to the cost or could be listed as a selling expense
Q3 - I received a K-1 that lists 2020 income. I'm paying taxes on the income, but I received no 2020 distribution so I believe the fact I received no distribution means that the income is added to my basis so I'm not double taxed. Is this correct? Example, invested 10K for shares, had additional income of $20K over years prior to 2020 for which I did not receive distributions meaning I entered 2020 w/ $30K basis. K-1 shows I have $50K in income in 2020 (no distribution). Current basis as reported by company (on shareholder basis worksheet received w/ K-1 is $80K (reflecting start of 30K + 50K in income). Sold shares for $100K which means I have a $20K gain not counting expenses in Q2. Am I reporting this correctly with this approach?
you nailed it.
