I don't have much problem switching between ortho and staggered. My guesses for why it's not a hassle for me:
1. I've got 2 work laptops, personal computers, and a lot of different keyboards, ortho and row-staggered. I switch between them and mix things up often. Maybe the frequent switching is good?
2. On top of that, I switch between Qwerty and Dvorak on row staggered keyboards pretty often. When I decided to learn Dvorak, it was really painful for the first month, but eventually I got my muscle memory for it working, and things are fine now. The experience of learning Dvorak "cold turkey" with blank keycaps gave me a really strong touch typing skill. I'm not saying you need to learn Dvorak, but forcing yourself into something new that really ingrains it into you, that's probably going to help you with being able to switch easily between a laptop and ortho keyboard too.
3. My ortho layout is completely customized. It's very Dvorak centric and only needs 33-keys, so it's adaptable between different boards. Keeping things so controlled minimal presents the advantage keeping things easy to remember. Also, because a small layout is so different, it really makes typing on an ortho layout (for me) a very different experience than a regular ANSI layout. Keeping those types of experiences so different prevents me from getting into situations where my muscle memoy gets confused on various layouts. It's like I've just developed a personal "ortho mode" or something... So that's something to consider too.
On a related note, there's a possibility of having a ThinkPad T460s/T470s with an ortholinear keyboard. Gotta keep an eye on this:
https://github.com/saoto28/pineapple60