Welcome, mastertheone!
Sounds like pumping and jelqing might be a good routine. You would not need to jelq in the ‘couple of hundreds’ range, and certainly not to start with.
Regrading time of day for your routine, this is from a previous post of mine on the subject:
Lampwick - PE night or morning What is better
The first priority is to find a time when you can do PE, and then do it consistently. Doing PE consistently is more important than a hypothetical optimal time that doesn’t consistently work in your schedule.
I think that PE just before bedtime is a good idea. I think that the natural cycle of erections during the night reinforces the stretching and expansion of PE.
I think PE in the morning right after you get up is a good idea. Your penis is warm and has been getting some stretching already through your nocturnal erections, so you are starting with the advantage of a well-warmed up unit.
But the most important thing is to do it, and do it consistently.
(It doesn’t have to be the same time every time, by the way.)