Well the business model of wise is that they keep large currency positions in individual countries so that they can avoid international money transfers. So it is by no means a guranteed international money transfer.
no, guaranteed entry with a visa does not exist. Immigration even with a visa has the right to refuse you entry. On whatever grounds they come up with.
If you bought the ticket as a multi city ticket on one booking, you do not have to pass immigration. In case of seperate tickets you have to pass immigration, collect your luggage andere check in again.
even two border runs will be problematic if you extend them with 30 days. see replys to post of amy wang from june 7th. immigration has become though in recent years since the june last year.