The current way to add the same place to your trip more than once is to click the + button and in the "Add a place" search bar, type the place's name the same way as it appears in the trip already and select it to add it again. While this works well for some POIs like national parks or museums, it can be tricky or impossible for find the same chain hotel in the search results and add it to your trip again. Here's an example. If you want to add Fairfield Inn & Suites in Virgin, UT to your trip more than once because you're staying at that hotel multiple nights - you cannot add it again by clicking the pin on the map or by going to the POI page on Roadtrippers because it's already on their trip. So they only way to add it again is by clicking + to search for it, but if it's a chain, it's hard to get the right one returned in search results. Here's the screenshot of all the options when typing the name of the hotel in the search bar. It would be great if the waypoint details window (where you can add a date/note) also had an option to add the place as a waypoint again, it'd be much easier than trying to search for it.
