I just started selling and trading shoes online and I deal with the same problems.

Acquire appropriate packaging

For packaging I try to keep boxes from Amazon orders and use those for shipping. You can also buy packaging supplies from eBay. This will be most useful for you if you’re selling a lot of items that are roughly the same size because they sell you them in bulk. You can get eBay tape, tissue paper, stickers, and all kinds of packaging options. You can also get free packaging from the carrier but if you’re selling something expensive this might not be the right choice because they are the ones who package the item for you. If you’re returning a package this might be the best option.

I usually google the dimensions of the item I am looking to ship and go from there. If nothing shows up I roughly measure using my phone as a ruler. It’s not a perfect method by any means but it works for me. For weighing an item, you can purchase a talking scale or if you have a normal scale already you can use the be my eyes app and have them read it for you. If you’re selling a popular item on eBay it will already have an estimated weight for you.

Preparing shipment.

When I print a shipping label I just fold the paper in half because the label is usually on one side of the paper anyways. I don’t bother cutting the label because it’s going to get taped down. To know which way the label is oriented you could also use be my eyes for that. You should put your label somewhere easy to find. I always use the top left corner on the top section of the box. I tape the label down with clear scotch tape because I don’t have to worry about blocking any letters or barcode. I tape around the four edges or the label as if I were making a frame for the label.

To cover old addresses you could use the new label and put it over the old one. I usually peel any stickers off of the packaging with a knife to make sure there’s no unwanted labels on the box.

An alternative to all of this is getting a label printed for you at the shipping facility. This is especially useful for returns because they will repackage the item for you so you don’t have to worry about old labels. All you have to do is get a QR code scanned. You can also give them your tracking number and they can pull up your label from the system.

Drop off at FedEx / UPS

I struggle the most with this. My UPS is too close to take the bus but too far to walk. I also don’t feel safe carrying a box and using a cane around my neighborhood. I always get a ride but those are hard to come by. When selling on eBay you can set your handling time to give you more time to ship out items. If you’re doing a return it’s much harder to be flexible though.

Scheduled home pickup

I’ve never tried this because it also confuses me. It costs money but it doesn’t feel fair because the UPS is less than 2 miles away. Like you mentioned, it would be nice to have a free and if not at least a discounted option for us who can’t drive.

I'm in the UK here, but I do a lot of selling with 0 sight.
my kitchen scale weighs up to 5KG; anything heavier goes on the bathroom one. I have a tactile measuring tape, although there's a measure app on my phone I think so it's just habit I expect. I source packaging material from stationery suppliers online. Couriers either want A4 printed labels affixed to packages (which I use an app to read so I know which is the right-side up) or addresses which I produce using a label printer, the back side of which is adhesive. Our national postal service will collect or there are any number of courier companies, some of whom will bring their own labels even.