Similar problems come up with anchored tanks and stacks.
One problem is that people want to over-analyze it. The appoach used in the tank codes is to assume that stress distribution in the tank/stack is Mc/I, and then assume that anchor loading must be distributed similarly, so the anchors are just treated as a ring of metal of equivalent area. And this seems to be carried to its logical conclusion in the large transmission towers that are supported by the bolts, with no contact between the base plate and concrete.
The alternate approach is to take a section immediately below the surface of the concrete, and analyze it as a composite steel-concrete section, and derive the anchor distribution from that assumption. The flaw is that anchor loading immediately above the concrete must be the same as immediately below the concrete, so making assumptions that give you different numbers above and below doesn't really gain anything other than complication.
In the case of your right-hand sketch, I think the flaw is that you have no rational basis to determine that triangular loading. In fact, the base plate is flexible and 2-dimensional, and contact stresses would very across the face, not just linearly along an axis. There is also going to be SOME amount of bolt pretension, and that unknown amount of pretension will also result in a distribution of contact stresses across the bolt area. So you can make one assumption and calculate bolt loads simply. You can make a different assumption and work through a bunch of math and come up with a bolt load, but it's still based on your assumptions. It's not immediately clear if you've gained anything by the complication in that case.
Two solutions come to mind. One is to refer to standards governing the type of construction, and see if there is a codified approach. This won't necessarily be more accurate than whatever solution you derive on your own, but using a method and an allowable stress that have proven to be satisfactory is an acceptable approach, even if the theory leaves something to be desired. The second solution is to support the base plate on the bolts, which simplifies the problem. There are many cases where it is easier to change the geometry to fit the math than the other way around.