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Your strategies seem to be good ones.  But the risk is still pretty small overall.  Something like a secuestro exprés is still possible where you are forced to accompany the thieves as they empty your accounts from ATMs.

Always staying alert, don't engage with strangers, situational awareness, no dar papaya, going out in groups with the family/friends,  all can help reduce risk but not eliminate it.

@stealtannest3t

Like @OsageArcher said, it sounds like you're basically prepared. If you wanted to reduce your risk even further, I'd HIGHLY recommend:

1. Avoid the street girls entirely
2. If you meet any woman from Tinder or other dating apps, vet them as best as you can before hooking up.
3. If, after meeting them at a cafe, vetting them, etc. and you DO bring her to your crib... bring ONLY her (no friends), and make sure the portero is aware (make her show ID, etc) and make sure she isn't allowed to leave without being accompanied by you.
4. Before you bring anyone over, secure your valuables. No laptop, gadgets, loose cash, etc. lying around.
5. If possible, she should come without her purse. But if she DOES bring her purse, make her leave it somewhere she cannot easily reach, like, at the door or something.
6. This goes without saying but... always use protection (condoms).

Maybe this sounds like a lot, but once you get the hang of it, setting your boundaries early will help you avoid the hardcore "opportunistic" criminals who are really just looking for an easy target (once they see you have your sh!t on lock and you're not one of those Dumb Medellin Crypto-Passport-Bros who're just BEGGING to be scoped & robbed, they'll lose interest, AKA "weed themselves out"). So, don't make it easy for them.

By the way, if you just want sex (as the Basic Human Need that it is) without having to think about all this stuff, and you don't care if the experience is "warm lover" or "cold fish", then it's better to just go to a brothel. Sure, there'll be no illusion of actual attraction or passion, no passionate mouth-kissing, and some workers are "cold" (or just tired)... but at least you won't have to worry about safety and theft. And if you're nice and charming enough, and you happen to pick a sweet, not-yet-jaded worker who genuinely enjoys sex (or is good at acting), you might STILL get a "warm" experience. It's worth a shot.

In any case, be safe, and good luck!

@ ChineduOpara - From your lips to God's ears! Spot on.

My very first visit and extended 4 month stay was to Bogota in November of 1990, those were different times for sure.

Fast forward 35 years and been living the past 10 YEARS right outside Medellin and over these past 35 years I too have been no saint but ALWAYS have kept the basics of "situational awareness" as you laid out as second nature, so far going good!

I could write a book about what I have personally experienced, what I have observed from others and the changes over the decades that now puts such a stain on what a decades ago would have been a much less effortless visit to Medellin than what it has evolved into.