Siding Problems - Need Recommendation

[Bradley Dosch]

Could someone please help with the following situation. See Google drive for pics: 

https://drive.google.com/file/...

My house was built in 1971 and has the original composite wood siding. From the pictures, there are certainly places with damage but I'd say the majority is in decent condition.

I am currently house hacking this house but plan to move out soon and turn it into a long term rental property. It is a single family house near Denver in a suburban neighborhood.

My original plan was just to have a contractor spot fix the places in the pictures. However, after talking to more people I am considering changing the entire siding. I am trying to figure out if this is worth it.

I have been told the most cost effective, long term solution is to put vinyl siding over the current composite wood siding. They would put a layer of insulation in between.

I like this idea because it seems like it will be low maintenance and really take care of the problem rather than just putting a band aid on it. I also love the look, price and durability of vinyl siding. My biggest concern is that I am over improving. Does anyone feel that this would be over improving? Of course, the price is substantial too – looking around $12k.

Anyway, this is a really big decision for me and I would really appreciate anyone being able to give any insight! Thank you so much