You do not need special stuff for quality leather shoe care.

1. 2 Gallon size plastic ziploc bags (Sharpie one black and one other)
2. 2 horsehair buffing brushes
3. 2 horsehair daubers AKA polish application brushes
4. 1 container of edge dressing
5. 2 cans of polish (Kiwi Black and Kiwi Neutral)
6. A bunch of buffing cloths (honker pack of microfibers)

You can get all the above from eBay for crazy cheap. Make you a black shoe kit and a brown shoe kit. You can use neutral shoe polish on every flavor of brown shoe as there are 934,893 shades of brown shoes and 63,214 shade of brown shoe polish and they odds of you getting a match are near zero. You can even skip the daubers and use old tooth brushes or sacrificial cloths. Don't mix up the kits as you don't want to blacken up your brown shoes. You polish your shoes every 3-6 months and perhaps buff when you see them getting dull. Youtube has an infinity of videos on how to do it.

Cobblers are a thing. You can take your shoes there and say, "Make deez good". Return in 1-5 days and for $20 and zero effort, you have nicely cleaned and polished shoes.

Anything you apply to make your shoes waterproof is a lie. Shoes are natively waterproof based on construction/materials, not some goo you rub/spray on. If you want waterproof shoes, but them out the gate that way.

You can wear for days in a row. Allowing them to rest is smart and will increase the lifespan and split toe shoe trees will help keep the shape when not worn. Rest is best practice, not a requirement.

GYW shoes can last your literal lifetime. I have two pair from the 80s. The real sweet spot is around $300 pricepoint for men. Anything less is lower tier. There is no such thing as break even point as that talks to your desires and budget and we know neither.