I’m not often impressed with safety fencing and or self closing self latching mechanisms ... but overall, I am very pleased with what I see here. Sturdy and well thought, and likely will last a VERY long time without much attention, except the pin latch pin itself (in 1 - 25 years?).

Pool Surface
The plaster surface shows noticeable wear common for a 15–25 year old finish (22 years). It is in fair overall condition overall for its age but is noticeable a bit more abrasive, which allows organic matter to grow more easily, but nothing too substantial beyond general blemishes and wear markings, especially on the bottom and in the deep end and corners.

The main drain looks like it has been updated or repaired at some point (likely original) with a noticeable seam, but no additional cracks are visible outside of that seam. There are many unusual blemish marks (more than 100), making it difficult to distinguish cracks, but scratches are seen (likely from dogs), but I do not see any clear crack-related damage issues which is ideal, but
one or two potential delamination cracks appear on the shallow end steps (deepest step on the northwest side) and there is a blemish or possible calcium fissure on the face of the deep end step (northwest side). These are generally expected with age and even though are not neededing to be repaired at this time - a full re-plastering, would address both issues.

With good maintenance, the surface likely has about 10 years of life remaining (possibly less than 5 years if not maintained well).
For a pool this size, full replastering would likely cost between $10,000 and $14,000 or more depending on surface options.

Waterline Tile
The waterline tile is missing in some locations, most notably on the west side and north side of the pool. Additional locations of concern are likely present (such as the south-middle side), where gaps are beginning to form.
It is likely that all the tile will need to be re-adhered with new mortar, especially the loose areas. If only about half the linear footage needs re-mortaring and reapplication, the cost would run around $1,000–$1,500. If re-tiling the entire pool, expect $1,500–$2,500 (possibly a little less since most tiles are still present and could be reused; new matching tiles, if needed, would cost less than $100).

There is also a lot of wear seen in the skimmer throat due for some updates soon ($500+)
The connected coping is in relatively good condition overall. Some cracks and gaps are forming, especially on the edges. These can be filled for $500–$1,000 in service if desired, but they are not very noticeable and not a major concern at this time. The main issue with the coping is to re-adhere some of the potentially loose stones closest to the missing tile areas and in a few additional spots.
Cost summary (this section only)
• Tile re-adhering / mortar repair (partial): $1,000–$1,500
• Full waterline re-tiling: $1,500–$2,500
• Coping crack/gap filling: $500–$1,000
• Re-adhering loose coping stones: included in above estimates

Water Quality
Water quality is fair overall. No significant algae is visible, except on bottom and corners, since the chlorine is high, it could be masking some even more significant algae present = recommend treatments now vs in 30 days.

There are likely high phosphates in the water due to the large amounts of organic matter, on going. pH and alkalinity are also pretty high, suggesting some growth is occurring (also signs of algae present). Cyanuric acid and calcium hardness levels are ideal, especially for a pool without noticeable water loss = water loss is likely not present. But recommend rechecking chemistry in 1–30 days to confirm no water loss and performing phosphate treatments ASAP to prevent the pool from turning green this spring/summer. Treatments might cost less than $100 now vs $300 or more later if postponed (due to heat incoming).
Cost summary (this section only)
• Phosphate treatments: <$100-$300

Main Drain
The main drain is a side and a single specialty main drain designed to allow organic matter to be sucked in rather than just sit on top.

This (main drain in bottom center) would definitely not be my first choice, but may be a great option when seen over time).

In the future my rec might be to update the cover to a more closed off to organics style because I would not want the mass organic matter being sucked into the main drain area, potentially clogging it or overfilling the pump basket — which is exactly what we are finding right now (pump basket completely filled with debris). So to help correct this non ideal issue = ($500 in labor (diving / sourcing / installing the cover) for modification + the new retrofit updated cover cost $650 (direct from MFG at their cost)

The only way I would keep this current setup is by also installing an auxiliary leaf canister in between the suction line and the pump. This is a common in in floor cleaning setups where this exact type of main drain is used per design, and a much better solution for mass amounts of ongoing leaf debris, but it would likely cost an additional $1,000 to $2,000 in parts and labor to install that so comparable.

The determining factor will be to see just how much debris is being collected in the main drain / if it gets clogged easily / and if the pump gets clogged quickly (which I suspect it is already doing just that).

Cost summary (this section only)
• Auxiliary leaf canister installation: $1,000–$2,000
(Previous main drain cover update still applies: ~$100)

Skimmer
The skimmer could use a weighted basket for less than $50, a new float O-ring for less than $50, and a new skimmer lid for less than $50. For less than $150 total, this could be updated to a more ideal status.
This is especially important because the skimmer on this pool is the most important thing, as the pool gets a lot of leaf debris.
Cost summary (this section only)
• Skimmer updates (weighted basket, float O-ring, lid): <$150

Like new

Auto Fill
The auto fill is an MP style with a float. The canister appears to be in good condition with no major issues.

The fill float itself is due to be updated ($50) +

I also found a leaky threaded connection on the shut-off valve located on the side of the house near the access fence = It is in a tricky position to repair .... currently there appears to be a small bit of water loss present.

The total cost for the auto fill related repairs is expected to be around $250

Pool Light
The pool light is more than half filled with water (about 48% filled).
Recommend changing the pool light out ASAP. A new light can is around $300–$1,200 depending on options, plus around $400 to install any of those options.
It should immediately be removed from electricity if possible for less than $150 service call, or just by simply removing the three wires in the timer panel.
Cost summary (this section only)
• New light can + install: $700–$1,600 (depending on options)
• Immediate disconnection from electricity: <$150

Filter
The filter is a cartridge filter of good size for this pool. However, due to the massive amount of organic matter from overhanging trees, it gets impacted relatively quickly. This stresses the elements and the filter pump, causing higher pressures.
A sand filter would be a better choice for this heavy-debris pool. The Pentair TR 140 C is a strong option — it is fairly large and could fit in the current filter space if the main filter pump is moved. The pump is currently in an awkward location that makes weekly service and cleaning difficult. I am surprised the fitting going into the pump hasn’t broken yet.
Moving to a Pentair TR 140 C sand filter would be a wonderful upgrade, along with running a proper drainage pipe to an appropriate location. Cost for the TR 140 C: around $2,000 + ~$800 labor.
If continuing with the current cartridge filter, it appears to be nearing its due date for regular quarterly cleaning, so service is recommended now. Otherwise, no additional issues are visible with this filter. A quick coat of spray paint on the top (almond color to match) for UV protection would help the tank last a little longer — around $50.
Cost summary (this section only)
• Quarterly cartridge filter service: ~$100
• Spray paint for UV protection: ~$50
• New Pentair TR 140 C sand filter + labor + drainage: ~$2,800

Filter Pump
The filter pump is a WhisperFlo. It appears to be in usable, workable condition at this time.
Unfortunately, the motor bearings are very worn and causing significant noise. The motor is already running at a 3 out of 4 heat level, indicating it is highly stressed and overdue. I do not expect it to last longer than this next summer. It could potentially start a fire if left in its current condition much longer.
The motor itself could be swapped for $300 and up plus labor, but because there is so much wear and sun exposure on this pump, it may be wise to consider updating the entire pump instead (not required).
What is required right now is removing the induction line from the non-used ozone unit and simply capping it (less than $50). Updating the motor will likely range between $500 and $1,000+ with labor and is due in the next year before this motor will completely expire.
Cost summary (this section only)
• Ozone line cap: <$50
• Motor replacement + labor: $500–$1,000+
• Full pump replacement (recommended long-term): not estimated here (typically $1,100–$1,900 + install)

The panel is in fair workable condition, and the breakers all appeared to be operational however they are older and should be updated to GFCI for safety ($300+) otherwise no issues present.

Valves and Fittings
Everything appears to be in relatively good condition with no major issues in the valving. No additional leaks are visible other than the ones already mentioned on the filter pump.
All I would do is repaint and re-label the equipment pad for less than $100 and cover it from the sun using UV mesh for less than $50.
Otherwise, the system is in working condition.
Cost summary (this section only)
• Repaint and re-label equipment pad: <$100
• UV mesh cover: <$50