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OP, you've gotten very good advice here and I would recommend a tax accountant as well. And it is correct that the HELOC has nothing to do with the whole issue.
We have investment property we sold this year as well and most likely, even though we sold it for way less than we bought it for, it looks like we will still pay capital gains because of the cost basis due to depreciation, etc. We have a tax accountant who has done our taxes for the last 5 years. There is no way I'd want to figure it out ourselves - the first year I tried to do taxes for our LLC she ended up redoing them.....
Try using the online Turbo Tax. It will guide you through this and the rest of your taxes.
I'm sorry, but that is not a good suggestion for this situation. He needs professional help. If you have a headache you can try to treat yourself by taking aspirin. If you're coughing up blood, the time for self-diagnosis is over.
BTDT this past year.
I've always done our taxes and have always been able to figure out the "20,000" various forms,schedules and worksheets needed.
But, oh my....selling a long term residential rental (over 40 years) became a nightmare where "20,000" more forms and worksheets were needed.
You haven't been at it that long so won't run into some of the same problems but still, if you start out thinking the depreciation is something you can take 'off' and don't even have any idea of whether or not it was ever taken, put your pencil down and hire somebody.
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