I don't often have the problem of soles wearing as I have so many pairs of shoes.
However I tend to wear the same 5 over and over, and recently I did pay to have a pair re-soled as the sole disintegrated and the company sent me new soles and I just had to pay for the workmanship which WAS $85!
However these shoes cost about $230 to buy new so I figured it was worth it.
I will sometimes have shoes re-heeled as that is not so expensive but only if they are expensive, or very comfortable shoes.
Resole/Repair — the cost and time it takes are relative to what you originally paid for them. I can't justify spending more than ~$150 on a pair of shoes, I try to buy them on sale, to get a $200+ pr for my budget. If I have a $50pr I wouldn't bother, if my $100-150 shoes start wearing thin or the heel comes astray, I would get them resoled, but probably not a second or third time, as by then other stitching is liable to start splitting, and the inner sole will have worn through numerous times by then, and possibly the lining lifts, a good shoe repairer could fix all those. I you keep shoes dry, and alternate wearing them with 2-3 other pairs, they will last several times longer (up to 5-10years), whereas a pair worn day-after-day could need replacing 2-3times a year. Repairs will help them last, but not as much as replacement.
I always used to get my shoes repaired/resoled when I was younger,as I had some extremely comfortable ones which,by the time they needed some work,were no longer available to buy new again! I now wear extremely comfortable 'Orthaheels' in various styles and colours ,and these do last extremely well,as well as being a very reasonable price for me as I buy them when they are on sale!! When I was in my last 5 years of employment,I found the same true of my Homy Ped shoes which I would love wearing to work,as I would be on my feet most of the day.I would buy these when on special,as well,so they were very economical. Even so,with my absolute favourite ones,I would get those repaired by 'The Town Cobbler',who would have to be one of a dying breed of tradespeople nowadays!!! He would take the most incredible care to return my shoes looking like brand new!!
I never have to re-sole as the leather upper wears out. I wear orthotics and as they are expensive I wear the same pair every day so I more than get my money's worth out of a pair of good quality shoes.
Definitely get my good shoes and boots repaired as they are purchased with care in the beginning...and I have trouble getting a wide fashionable fitting so this way they last longer...and save me money the long run...
I must admit to discarding my shoes when no longer wearable. Your question has however conjured up a childhood memory....my parents tracing the shoe outline on a piece of cardboard (an empty cornflakes box for example) and fitting 2 widths of the cardboard cutout inside our shoes if the sole had a hole in it. This may be hard for younger readers to image but people became very resourceful back then when money was scant.
Gosh, I remember doing this as a kid in England. It's sort of sad really, as it wouldn't do much in the rain or snow but it was therapeutic, I imagine, doing things like that after the war. My mother was still putting blackouts on the windows 10 years or more after the war.
I’d rather have a pr of shoes re-soled, if need be, because I’d already worn then in, but some shoes just aren’t able to be re-soled, & even the boot maker has remarked, “Sorry, it’s just not worth re-soling these shoes".
I buy Lloyd men's shoes to wear to work which are +$300 and given I keep them in good condition they can last a long time. I had a pair resoled 4 years ago that I bought in 2001 in Europe and the uppers still look fantastic so they were worth getting resoled. I buy timeless looking shoes not garish things with buckles so they don't really look out of fashion years later.
So definitely yes if they are good shoes as it is then worth it.