Start with why Hakone is in the route
Hakone is a pacing decision, not just a place to sleep between Tokyo and Kyoto. If the point is onsen, ryokan dinner and recovery, the stay needs to carry the experience.
Ryokan
Choose a ryokan when the evening and morning matter as much as sightseeing. Arrive early, keep the day lighter and let the stay be the main event.
Onsen hotel
Choose an onsen hotel when you want baths and comfort with simpler logistics, especially with children, later arrival or a less formal rhythm.
Location
Hakone-Yumoto is easiest for arrival and departure. Gora works well for museums and the mountain railway. Lake Ashi suits views and a slower evening, but adds friction.
Day trip
A day trip is enough if onsen is not central, Tokyo time is short or you want a limited loop. It gives movement and scenery, not the same rest as an overnight stay.
When to get personal help
Personal planning is useful if you are choosing between Hakone, Nikko, Kamakura and an extra Tokyo day, or trying to add a ryokan night without making the route stiff.