A single antibody test at 6-8 weeks would be sufficient in this situation. If you get more than one test, do it twice, at 1 and 3 months. You can expect negative results.
If your sexual behavior and choices bother you, counseling is a good idea. Congratulations for recognizing and dealing with it.
Welcome to the forum. I'll try to help.
Some aspects of your story indicate high risk for HIV, others low risk. Certainly your partners were at high risk. Not all sex workers are, but street walkers tend to be at high risk. And if you have genital herpes due to HSV-2, your risk is higher than otherwise; and the risk appears to be especially high if someone is exposed to both viruses and catches HIV and HSV-2 at the same time. On the low risk side, you used condoms for all the exposures, and condoms are highly protective.
You don't describe how the diagnosis or genital herpes was made. Your description doesn't sound much like herpes. The rash on your thighs was definitely not herpes, and a single penile sore is unusual for the first HSV infection. If you do have HSV-2, you might have had it before the sexual exposures you describe.
To the specific questions:
1) The chance of catching HIV while wearing a condom is very low, regardless of other lesions on the penis. The penile lesion might have elevated the risk, especially if it was due to herpes -- but the odds still are strongly in your favor.
2) I cannot comment on one SW's skin lesions. Certainly the ones on the thigh and knee are not of concern; those are unusual locations for herpes lesions. I suppose the oral lesion could have been herpes, but only HSV-2 is associated with increased risk of HIV transmission; HSV-1 (which causes the vast majority of oral herpes) is not.
3) All things considered, the risks are high enough for you to be tested to be sure you didn't catch HIV. But as I said above, the odds are strongly in your favor. The chance you caught HIV probably is less than 1 in several thousand.
I hope this helps. Best wishes-- HHH, MD
I wish to add that I of course will get HIV tested, realize it needs to be done at 30, 60, and 90 days. I also have started counseling so I do not engage in risky behavior again.