Closely spaced pear pictures plus some "umbrella" pruned trees

This is certainly A possibility. That they will behave as a single tree. I just have not seen it .only several Chestnut plannings that were crowding their neighbors and unproductive because of that situation,.
If these grow together and are allowed to develop a good full canopy , it may work ?
@scottfsmith definitely has more experience growing trees in a tightly packed space than I do. I have plenty of room here. I try to give each tree appropriate space . Have a few in the same hole , where I planted a extra next to one that I gave up for dead, but both lived .
Those trees don’t seem to thrive , hard to chose which one should stay / go sometimes ?