I Can totally relate to these stories in that I am in the same boat
As one cruiser with a lot of experience told me
"Go small and carry Green Luggage"
Bigger boats are great for the room but considering moorage fees
and the crew to handle them you are so far ahead if you go with a smaller seaworthy boat
and bring enough money
to enjoy yourself.
I know someone who followed this mantra and bough them selves a Norsea 27. As the worked their way down to Panama
from San Diego
they found affordable moorages everywhere they went and if they decided then needed to pamper themselves they booked a room in a hotel
and used their amenities to wash their clothes, get cleaned up and enjoy the hotels amenities.