Aloe, Haworthia and Gasteria are three genera which are related closely enough to allow crossing among them. However, I have never encountered a cross between a large genotype (e.g. Aloe Ferox) and a small one (e.g. Haworthia cooperi).

By small or large I mean the size a plant can attain, at or close to its size limit. In the case of members of the Aloe family, it's about the size a single rosette/offset may attain: That's when the rosettes/offsets multiply without increasing their size.

Is pollination possible between two specimes differing greatly in size?

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The deciding factor is if the two plants are closely related enough to successfully hybridize.

Assuming you have a close enough match between two dis-similarly sized plants there needs to be a transfer of genetic material. If you do it yourself with a paint brush, problem solved! If you are expecting "nature" to do it, here is where you may run into challenges.

First you need a common pollinator that will visit both plants. Then the flowers must both be capable of giving/receiving pollen from the pollinator.

Flower structure, time of day the flowers are open/closed, time of year for blooms from your two plants, all impact the likelihood of success.

Specifically with Aloe, in 2013 there was a fairly significant shake up of the Aloe taxonomy based on genetic study, so that plants formerly named aloe may not be as closely related as it seemed.

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