Driveway painted, repair needed.
 

Does anyone know a company that specializes in driveway paint repairs? 2 small areas, maybe total of 3 or 4 sq ft.

Most of the local companies will not touch this type of work due to liability issues. All will probably require the entire old finish be removed and then the new finish can be applied. This is especially if the driveway is actually "painted". Real "paint" does not hold up well in the Florida sun on concrete. If it is "stained" you might get lucky and find a suitable match at Sherwin Williams with the HC xylene based stains. If you are not interested in the cost to strip the driveway ($2 to $3 per square foot), and then the cost of the new finish, you might try the DIY or handyman repair.
IMHO, if you decide to go DIY, get a quart of the Xylene based product and coat a test area, if it works, clean the entire driveway, make sure it is nice and dry and coat the entire driveway.
Hope this helps.

On a somewhat related note, our driveway stain job has held up extremely well, but we have developed a couple stress cracks that I would like to have repaired. Wondering if anyone else has experienced this, and if so, how it was repaired?

Ugh, I'm in the due diligence period of all this sort of thing right now. My driveway has several longish cracks and I wish there was a way to just repair them but, I've now had two experienced concrete contractors tell me, "there's no product or technique that can adequately repair concrete cracks for any duration".

My driveway also has other issues and is 35 years old so, I'm resigned to installing a new one. It's not the worst outcome because I wanted to widen it a bit anyhow.

Separately, a concrete decorative contractor that's done plenty of work in TV gave me a quote of $1.25 per sq ft to grind off the existing coating. Edison ConCreations Inc. - Home

Shortly after we bought our house (2013), I used a 25 year rated caulk to fill all of the stress cuts in the driveway. I did this to stop the weeds and it worked perfectly. The caulk is flexible and seemed to fill the cuts very well. This did not work as well sealing the area between the driveway and the landscaping wall, it appears the wall moved more than the caulk could handle. I give you this info as it may provide a suitable way to extend the life of the driveway. Send me a PM if you would like to discuss further over the phone.

All though this is grey this is one example of caulking you can use. For the low cost why not try it before going to extreme measures. I would ask Home Depot, Lowes or Ace Hardware people when your there for advice.

I used the flex seal caulk to fill in the stress cracks on our pool deck about three years ago and it has held up perfectly. It can be painted with the exact match acrylic deck coating T&D originally used on the decking (available from Florida Paints located behind Culver’s). The problem with using that on our driveway is that I have no idea if and/or how it can be treated to match the rest of our stained driveway. I guess I’ll have to contact Amy Newsome (she stained and sealed our driveway) and ask her about that. I need to contact her anyways since she did our driveway almost 5 years ago and it’s getting due to be resealed. As always, thanks for the advice.