Rearranging buttons is doable on the Xsight, but it is a pain. On harmony, of course you have those blasted arrows. The easiest way around that is to delete a button and add back the one you would have moved. This method (delete and add back) works fine for moving buttons from one page to another on the Xsight as well (within the same page you can drag to move them around). The hardest thing to get used to is when adding buttons, they are done in reverse order. So you have to plan your button layout carefully to avoid a lot of rework. JP1 is a breeze compared to harmony and Xsight since you just drag and drop functions onto any buttons you want. They run about $15 (or $1 and up on ebay). However the programming interface cable is $30 unless you build it yourself. An unlike harmony or xsight, there is no LCD, so all functions must go on hard buttons. Luckily you can put multiple functions on one button (primary, shifted, long press, double press, etc.), but it is difficult to remember what function went where. I usually have to print cheat sheets for my JP1 remotes, which is easily done in the software.
1) Saving your learns is tricky, but they aren't wiped out if you do it right. I don't remember the details, but there is a way to sync your learns so they go in your web profile. But the order of events is important. I and others have written detailed procedures for doing this correctly, so you should be able to find it.
2) I think it's a real issue. I've had many harmonys and all have had failed buttons within a fairly short time, especially the often used ones like volume. I think it's a poor design of the metal dome contacts. The 700 seems to be done differently and has held up much better than my 500 series did. The One and 900 may hold up better too, but are very expensive. Cheaper remotes that simply use membrane keypads hold up much better and can simply be cleaned to bring back to new condition after several years.