Hi sleepyface,
I would say you’re definitely on the right track.
In general … latex is such a durable material that even in a mattress which is one sided … it makes a very good choice.
A pillowtop is generally an extra layer of foam on top of a firmer mattress that also contains some foam and really means a separate “pillow” that is attached to a firmer mattress. The pillowtop itself is not as big an issue as the materials that are actually in the extra “pillow”. If it’s latex (and the pillowtop doesn’t make the comfort layers too thick for your circumstances) then a pillowtop would be fine. In other words the thickness of the top layers as a whole (including the pillowtop or without a pillowtop) and the materials that are used are the most important. A pillowtop can be made a little softer than a “tight top” which has the same amount of material because the pillow acts more as an independent layer (something like a topper but not as much).
While most mattress materials do better with two sided construction … and it will even extend the life of a latex mattress and any quilting fibers or foam that is on top of a mattress … it’s not as necessary with the most durable materials such as latex and would become a “value” choice rather than a “necessary” choice. I would also feel free to experiment with latex comfort layers over latex, innerspring, and higher quality polyfoam support cores depending on your budget and on your preferences.
Combination side and stomach sleepers have a particularly difficult challenge. Side sleeping needs softer thicker comfort layers to relieve pressure while stomach sleepers need the opposite with firmer/thinner comfort layers to prevent sleeping in a swayback position which can cause back issues. The “best” approach is generally to choose the least thick and soft comfort layers that provide good pressure relief on your side so that your are closer to the support layers for better alignment on your stomach.
I’m guessing you already have but a good place to start is the overviews in the mattresses section of the site. I would browse them rather than “study” them with a goal of being able to ask better questions rather than becoming an “expert”. While even this will give you more knowledge than many more “mainstream” outlets, the better outlets will usually have a lot more “accurate” knowledge and experience and with your better questions in combination with their willingness to help someone who has done some homework … you can make much better choices. Of course there’s lots more detailed information on the site if you choose to go in that direction.
There is a Toronto and GTA thread here which has quite a few of the better options in the GTA and some information and feedback from a few members as well. Feel free to post any feedback from your experiences and also to post any questions along the way :).
Phoenix