1st things 1st, if you met your guide here, I hope it is somebody with a lot of credibility in this forum, and not some random person with no history. Assuming he is credible, here my thoughts:
It sounds like you have most of it figured out. What it really comes down to is how much you are paying the guide per hour. If it is a flat-rate per 8hrs, or if it is per hour? Also the price per hour matters.
Depending on the cost, with an already-paid-for driver, I might do
- Guatapé/El Peñol
- Parapente (Paragliding) in San Felix --- best single experience in Medellín, after the dynamite pussy, of course!
- Downtown walking/bike tour
- Comuna 13
- Etc.
You could technically UBER to San Felix, but given traffic, a guide may be cheaper. Again, it depends on how much they are charging you. My Package that I bought included transportation both from, and back to my hotel. It was cheaper that way anyhow. This goes 3x for Guatapé. It is probably cheaper to get a package then hire a private driver.
If I only had 4 days though, I'd probably do Parapente, and Comuna 13. Guatapé is far and requires most of the day. Perhaps hit it next time. The downtown walking tour would be cool, but again, you don't have a lot of time and need a least one day for a casa tour.
Another thing, if your guide is mostly focused on adult activities, they might not show the tour of Comuna 13/downtown as well as somebody who really can deliver the story well.
So now, I'm just going to assume he is more of an adult focused guide, so you probably just want to do those other things as part of a package with formal tour operators to save money.
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With my adult guide, I definitely hit the casas and maybe La Isla/Fase2 at night. The casas are the most work/time/effort/etc. They are worth it, but between travel, locating the address, knocking on a random door, etc. you will get the most return on your money for having a guide.
You probably know from other posts that Ellas Erotic, Angeles, Eclipse, Chicas Plus, Geisha, The Garden, Golden House, and Instinto are some of the more popular houses. For specific girl recs, you can search the forum, or your guide can help you with that.
For night tours, the only qualification is that make sure you don't get gringo priced. Your guide should help you with that, of course, but clubs have been known to triple the cover charge are force you to buy a bottle even if you are alone.
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Restaurants
As always, it depends on what you like. Also, what area you will be staying in, but here are a few.
Higher-end - these are a mix of foreign as well as Colombian influenced/fusion restaurants
- Carmen Group
- Carmen, Don Diablo, Moshi
- Chef Juanma(El Cielo): El Cielo is amazing, but in the same hotel he has two other restaurants too: La Sere & El Bistró.
- Outside the hotel he has Kaime (vegetarian), and Cuon
- Mamba Negra - not what it used to be but if you want decent food with a great "Vibe/View/Etc." this is a decent option
- Colosal - very popular, especially with locals. the original "with a view" restaurant. happens to be right by Loutron.
- Sambombi
- Alambique - a fun/quirky place
- Oci.Mde
- In Situ
- Idílico
- Ritwal
- Marmaleo
- Babette Woodfire Bistro
- ...tons of other around Provenza, etc. It would be easier if you had a specific type of food you wanted to try and we could narrow it down.
Local Cuisine - every colombian is going to have their own favorite, but here are a few:
- Hato Viejo - a slightly more upscale (but still reasonable) version of traditional colombian cuisine
- El Rancherito - solid, mentioned to me by multiple locals (where I went, was great)
- Sancho Paisa - a favorite of one of my local guides/friends
- El Gloria de Gloria (in Envigado) - known for huge chicharron
- Mondongo's - known for Mondongo (of course)
- Ajiacos Y Mondongos - like the name says
- Doña Rosa - another local favorite
Misc
- Bramante - some of the most popular burgers
- Rituales (Laureles) - best coffee IMO. They have a little sampler so you can try all of their locally grown/roasted blends.
- Other decent coffee was at Pergamino, Hija Mia, etc.
- Cafe Cliche (Laureles) - might be closed for now, but if it is open, best "Menu Del Dia" I had.
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Let us know if you have any follow up questions. And PLEASE report back with how the tour was, what you did, etc.
