RollerPigeon, there are many considerations, including financial, but first, how much iron is there in your well? And is it a deep well with a good aquifer, or have others in your neighborhood had problems?
Do you have a whole home softener?
Do you have a seasonal, above ground pool, a seasonal inground pool, or do you plan to stay open-all-year? How many gallons?
Would trucking water compromise your finances? Eg. You can buy a lot of filters and metal sequestrant for $1,000...less up-front cost but more long term hassle to manage for sure..
Is any little stain going to drive you crazy, or will a semi-annual stain cleaning session not phase you too much?
We don't have nearly enough info to give you sound advice.
My well has 2 ppm iron. I now top up water via a dual softening system plumbed to an outdoor pool spigot. For a liner change, I did truck in $1000 worth of water

But stains bug me...
The thing most don't realize is that trucking in water to fill doesn't actually magically mean you won't have management issues later down the road because your top up water is still coming from that well. Eventually, if you don't manage the iron, you will slowly accumulate enough new iron from fills to need sequestrant, stain treatments, etc.
So whether you truck in water to prevent your well tapping out, etc., or not, you still need to know how much iron is in your well and consider options such as using metal sequestrant, prefiltering the hose water for marginal but meaningful reductions, etc. Tell us more and we can give you better advice more specific to your needs.
Update:
The national "average" loss via evaporation of pool water per day is 1/4 inch, or in a yearround setting, that would be an average of more than 90 inches lost per year...
However, rainfall might replenish much of that, depending on your location.National averages range from 9" to 63" per year, including snowfall. Other things to reduce evaporation, such as a solar cover, will help.
But in theory, $1000 of new water could, by this time next year, be composed of 50% (or more in a dry area) of your well water if you have normal evaporation and an annual rainfall of 45".
If your well had 2 ppm iron, by this time your pool would have 1 ppm...double the level that causes staining
This is why I feel that while often necessary for the health of a well, and to get a clean start, trucking water is no panacea longterm for people who have pools with wells high in iron
Hope that makes sense.