Winstrol is generally not preferred for building mass as it is highly anabolic and very slightly androgenic, an oral Steroid such as Dianabol is usually a better choice for people wanting to bulk up. Due to its ability to dramatically lower SHBG it can be used in a bulking cycle as a means to make other hormones more efficient, increase free testosterone and even solidify gains to a stronger degree but most of the people will find other steroids to be far more beneficial than winstrol in the long run. However some people are very sensitive to side effects of certain Steroids such as Dianabol, and would rather use Winstrol in a bulking cycle, while the weight gain wont be as dramatic as with Dianabol, with a proper high calorie diet, you can still see good results.
Again, like the above question, the only person qualified to answer this question in your particular case is your doctor. There is a very good reason that you can’t buy “TRT kits” at the drugstore, its because there are a lot of issues to be weighed to know if the health benefits of TRT outweigh the risks of going on TRT and only a doctor is qualified to determine that. Having said that, in general terms, as I say in the answer to question 1 “Is TRT Legal”, TRT is used to treat some serious symptoms. The advantage of TRT is that it reduces or eliminates those symptoms. It will also help re-gain (not gain) muscle mass that was lost. What are the disadvantages? Again, discuss the health risks with your doctor but three indisputable disadvantages are: 1) the cost, 2) the inconvenience and 3) the fact that you would be on the medication for life.