Being on disability and in section 8 housing, making ends meet can be a challenge. If you have items that you want to sell, buying them in quantity allows you to determine a competitive market price that can beat what others might sell it for. Also, when you sell at flea markets, you don't need to be concerned with taxes. Selling items out of state keeps you from having to file taxes in your own state. Road trips are useful.
OfferUp will NOT be workng on behest of the tax collector anytime soon, unless it meets the following criteria (which...will not happen anytime soon):
1. TruYou for ALL users mandatory (a specific person has to responsible for the tax liablity).
2. Listing fees implemented (the selling price has to be accurate and static for the calculation of the appropriate sales tax).
Etsy and Amazon has been on the forefont on AUTOMATIC tax collections as only 3 states (WA, PA, and OK) have what is called marketplace facilitator sales tax implemented (usually for sales of $250K or more within a 12month/period). eBay has also started to collect on these 3 states this year, which I previsouly indicated within the forum.
There are 7 other states that have some sort of marketplace facilitator sales tax program, but these states leave it to the individual sellers to pay the taxes, unlike in the 3 states that make the "selling app" responsible for the tax collections.
There are 20 more states that will also have marketplace facilitator measures under consideration, but they all differ from state to state, but will most likely be implemented by the end of 2020.