Let's see what happens if we start you two pretty far away so Ashley has a turn or two to get her summons up. You both have all the equipment you have in the regular game, so that means Ashley can sit and hide behind her new shield and get cover, or a tree. Cat has 25 HP, Ashley has 10, so if you can get one or two hits on her she's done. Her AC is low too, but she has lots of minion potential.
The elevations here aren't much, don't worry about it. The squares are 5 ft. Cat gets to go first and you currently have a clear shot to Ashley. Keep in mind there is disadvantage if you're more then 150ft away. You are currently 150ft away
Ashley can summon with 1 or 2 summons on the field, she has 3MP and will transform into a Panther when she is at 0MP. Her summons do not normally share advantage/disadvantage with her except in instances where it makes sense like if she uses Tides of Chaos, all her summons will have advantage that turn.
Ashley Panther LVL2 has "Battle Ready" and no longer uses up her action to transform, so when she transforms Ashley panther gets her turn directly after, effectively giving her two turns, though one of those turns is the action that causes the transformation. Similarly, when she casts summon, her summon can take a turn immediately.
Ashley panther is technically on the Fighter tech tree. She had 18 HP and Action Surge once per rest. Keep in mind she can also disengage and hide on the same turn as bonus actions. So your real opponent is Ashley Panther, with an AC of 13, and 50 movement speed, she's going to be a very slippery foe.
[1d4=2] If she transforms, the transformation will be clean, she will not get tangled in her clothes (but she'll be wearing underwear and have a penalty to intimidation, but intimidation is irrelevant here.)
[Roll Initiative: Cat 1d20+1=6 Ashley 1d20=1] So much for Bear system luck, Cat goes first.]
