Q1. Krassis and Jonus say i have an hlc on krassis can i use both of these ablities to re roll up to 3 dice.

Q2. Can Howlrunners ability actvate more then once if more then one friendly ship is in range

Q1 - Yes. As long as you don't reroll the same dice more than once.

Q2 - Yes.

^ This.

And I've used Krassis with Jonus to great effect, with Krassis packing a RecSpec crew and an HLC too. I paired it with Howlrunner with Swarm too so Krassis was upped to PS 8, alway picked Focus action then fired and re-rolled up to 3 attack dice.

Yes to both questions.

Q1:

Note that you can use either ability first and look at the result before deciding whether or not to use the other ability.