how hard is it to add pool lights?

Adding them is a pretty intensive job. The shell will have to be cut or hammered out and the surrounding landscaping and/or decking will have to be removed in the areas. Then the shell will have to be repaired around the light niches and the landscaping/decking will have to be prepared. I don't have a guess as to the dollar amount, because costs vary around the country, but I'd say it'd cost about the same as having a skimmer replaced (X2).
 
If you install nicheless lights the installation is much easier and you won't need to worry about bonding the niche to the pool shell.

I've installed several of these during remodels where there was no damage to the pool or surrounding decking/hardscape. It's all going to depend on where you want the lights and what existing obstructions you'll need to work around.
 
Having watched our PB install nicheless lights in our new build, it seems like adding them to a remodel would be relatively straightforward. I'm assuming they'd use a core saw/bit of some sort to drill through the shell, run a sleeve, bond the sleeve to the shell, and then run conduit from the light back to your control panel. As mentioned above, the complexity and cost will depend on access to the back side of the shell as well as how the wiring can be routed to the control panel (i.e. does it have to run under existing decking/structures).
 
First thing.......how often will you and your family use the pool at night? Does it justify the work and the expense?
I have had my pool for 27 months now, I think it was used at night twice when we had people visiting, we just don't seem to use it at night.
 
The light closest to the house likely won't be possible without demo. What about installing a light at the opposite end of the pool as the existing light? That actually look feasible.

A SAM and regular pool light are basically the same thing and will require a niche to be installed.

A nicheless light is about 1.5" in diameter and only requires a 2" PVC sleeve to be installed through the shell where it then gets tied to the conduit run.

Pentair's version is the Globrite. All of the other manufacturers have a similar product as well.
 
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