Machamp is one of the best pokemons you can get right now, dragonite still being strong and probably is the best generalist
all of this is assuming you have candy and dust...and TMs, is my pov my taste
1 .- i would get him counter and power him up
2 .- i would just power him up not going to risk a miss TM with heavy slam
3.- TM for counter and power up
1.- I would TM for change the HB because it has DB i love that move because is so fast, it has kinda good cp but you could dust it a little bit to lvl 30+
2.- Hard to say, isnt above 80 but has nice legacy moveset which i love, depends
then depends
3.- dust it and change the SW into DT
4.- Hold it a little bit or use it as gym attacker with low cp or leave it in gyms has under 3000 cp or you could power it up till lvl 30
5.- Dust it and change if dont evolve and already tmed the 3rd one
or
1.- evolve dust tm
2.- evolve dust tm if didnt dust tm the 95 iv one number 3 above