New vinyl siding over old unknown siding

[Harold Rutila]

My primary residence is a 1942-built bungalow that had some additions constructed over the decades which followed. Somewhere in the mid-2010s, a flip happened. The house was re-sided with white vinyl siding, but now that it is getting hot out, the siding is looking worse and worse. It was definitely a DIY hack job if you ask me.

I can easily pull back the vinyl siding at the trim around my windows and doors, and what I see underneath is more white siding, stained from age and definitely harder than vinyl.

My first question is,what type of siding might this be?

The second question is, what are the risks associated with this type of installation, where the vinyl siding is installed as a sort of facade on the home? I am especially concerned about mold and rot risks from moisture getting trapped between the layers of siding, and having this damage the structure.

My final question is whether it would be worthwhile, over the course of the summer, to re-side the house so that there is no layering involved. Jeff from Home Renovision has a series on siding old homes on YouTube, which I have watched several times. I just want to determine if it is worth the effort first.

Thank you!