I'm going to shoot for losing 100 pounds in 6 months

Why not pursue TRT treatment through a medical provider until you're in a healthy place (bloodwork is good, weight has come off)?
Probably because he has an enlarged prostate, (and more importantly) an eGFR of ~40 and blood in his urine.
 
i'd like to get some recommendations. Don't do it doesn't count.

A cazillion guys are going to these clinics for TRT. I don't see how a little of that would hurt.
Generally it wouldn’t really hurt very much. But I would tread carefully since you already have a few minor complications.

If your free testosterone is low, a small dose could be helpful - But as Tomes pointed out, there should be a specific purpose for everything you take. If you don’t have have any symptoms of low T, or if you don’t hit the gym/exercise at least 3-5 days a week - I’d say the risk/reward for your purpose might not be worth it.

My biggest concern in your case would be aromatase, which could counteract any benefits for the purpose of losing fat/cause side effects.

In conclusion, I would recommend getting blood work done before you consider it. If your free T isn’t low, I would probably not add testosterone.

As @milos mentioned, anavar is a better fit for your purpose. 10-20mg per day (the damage from Anavar can more or less be compared to drinking a beer per 10mg). If you do though, you should check your T every 4-6 weeks and make sure it’s not getting suppressed, though it’s unlikely to be at that dose. I’d also test BP regularly.

I have already suggested I think 2 times steroids here, so I will not tell you not to do it, risks are there of course and you have to do your own research first, but what im suggesting for weight loss is the safest steroid around - Oxandrolone or maybe better use SARMS - Ostarine, Ostarine is even under research to be used with Semaglutide to prevent muscle loss. Anyway back to practical tips: get on TRT first and then add low dose Oxandrolone or low dose Ostarine, or you can combine both, since it’s you, the bravest lab rat around! ;) (just kidding OK)

By low dose I mean 10mg daily for both, Oxandrolone maybe can push up to 10mg 2x daily, take it for lets say 2 months max, after 1 month off, watch your liver blood tests while on.

If you are serious about it, you should also get a second opinion from @Bacchus

What I was doing was TRT with dose a little over the limit (150mg/week) + Oxandrolone 10mg 2x daily 6 weeks on and 1 month off. Right now I took a break from TRT to restore my natural test (its already back, I was on HCG the whole time) and im right now on Ostarine 10mg daily

EDIT: you mention before you have enlarge prostate, so you will have to take DHT blocker, dutasteride is the best, but do some more research and again @Bacchus can probably give you some tips too
i don’t have much to add to this, it’s a good and safe approach.

Adding an AI could have its benefits, but it can be a bit of a double edged sword as it takes some experience to regulate your estro “by feel” - and the effects of AIs can be quite reduced if your body fat is high.

If adding T, I would probably do a shorter ester and more frequent injections in order to minimize aromatase and quickly get it out of your system if you experience any side effects.
 

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