Selling personal property and receiving money from Insurance Claims

I’m having a difficult time determining how I should track Income for a couple of scenarios and welcome feedback. I treat income as a negative expense for the following scenarios, but I’m not sure if this is the best way to track it. Every time I philosophize these situations, I keep concluding that this is the “best” way to track these transactions:

  1. I often sell household items to either upgrade them or downsize. Examples: Sell a TV cause I no longer need it or sell a lawn mower and replace with a new model. For both of these scenarios, I don’t treat the proceeds as an Income transaction. Rather, I categorize it as whatever category the item is. “Household items” or “House Maintenance”, etc. What do you think about not treating the incoming money as treating this incoming money as a negative expense?

  2. I have a couple of supplemental insurance policies that pay me claims annually. My Critical Illness Policy plan pays me $50 per family member one time per year for health screenings. I make money with this policy every year cause I pay about $250 per year and receive about $350 per year. So, my 26 paycheck deductions are expenses, but my 7 $50 claims are negative expenses for the same category. Similar scenario for my Hospital Indemnity plan. I pay about $400 per year, but am receiving more than that this year due to child birth event. Should I consider these incomes negative expenses instead of positive incomes?

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I handle similar situations the same way. I also like to resell items I’ve used, and I like to categorize that sale in the category the purchase was in, to offset the cost of the replacement. I also get a much smaller ‘rebate’ from my health care if I go through a couple ‘wellness’ tasks. I categorize that the same as my healthcare deduction, so a year end report would show the true cost of my health insurance was the payments minus the rebate.


I know this was answered but I completely agree! Am currently in the midst of moving back to Australia, and have been selling my furniture and such on FB Marketplace - I’ve manually added all these cash transactions to Tiller under my Household - Furniture category, so I can see the overall spend across the year.

I do the same with employment reimbursement expenses, as I get paid a per diem for meals, but usually spend less. So by categorising them the same (and using tags to identify which trip) I can see how much money I’m making!