I always try to find a substitute I can either rent or borrow for those bigger items, especially if my trip is shorter than 2 weeks. Is there a cruiser you can rent or borrow? Sometimes the idea/fantasy of bringing that extra baggage, is not proportional to the personal utility you assume it will bring. A simpler substitute (like renting) will more often give the same benefits, even if you feel right now like it won’t. 95% of the time, traveling lighter has more hidden benefits for optionality then you’re ever aware of (from my experience). I can probably write an separate post on that too.
If taking a longer trip, maybe your personal cruiser is totally worth it though, unless you’re a professional skater and need only your wheels.
For toiletries, I always have these bad boys on hand: https://www.amazon.com/dp/B00076RC0S/?tag=thewire06-20&linkCode=xm2&ascsubtag=WC82781