We've been "half timers" for 10 years. Split between Ohio & Florida.
We started with a larger hose. Then moved to a smaller house and rented the bigger house. Then built a one bedroom apartment over the garage and moved into that and installed full hook-ups for the 5er to use as a guest room. And rented the smaller house too.
Last year when we returned from Florida my DW said, "It's such a chore moving in and out of the apartment, why don't we just stay in the camper?" So now we're doing that.
"Squatters" have moved into the apartment. And when our DIL graduates from nursing school we'll decide what to do with the apartment at that time.
We're probably the most reluctant cautious full timers you'll encounter. But it does show that you don't necessarily have to commit all at once.
We wound up with most of our assets in property. Not too bad, as it generates income. And with smart phones and online banking it's not any more difficult to manage the properties from Florida. They simply pay their rent to our bank account. Furnace repair, plumbing, septic tank cleaning is all handled over the phone any way.
When we leave we tell our tenants, "Don't make us come back here! Or we'll come back with an eviction notice!" (It's worked so far, rent's on time every month.)