I have a Kaisa Survivor at base and have the Pridestalker legend. If I play a Kinkou Initiate from hand, can I trigger Pridestalker's ability to give my Kaisa +1 might and then resolve Kinkou Initiate to draw a card now that my Kaisa is 5 might?

Yes, you can sequence these effects to draw a card with Kinkou Initiate.

When you play Kinkou Initiate, both its "When you play me" triggered ability and your Pridestalker (Rengar) legend ability trigger simultaneously because they share the same trigger condition ("When you play a unit").

As the controller of both abilities, you choose the order in which they are placed onto the chain (Rule 333.1). To ensure Kinkou Initiate draws a card, you should sequence them as follows:

1. Play Kinkou Initiate: It enters the battlefield.
2. Place Triggers on the Chain: You choose the order. Place the Kinkou Initiate ability on the chain first, then place the Pridestalker ability on top of it.
3. Resolution (LIFO - Last-In, First-Out):
   • The Pridestalker ability resolves first: You target your Kai'Sa, Survivor and give it +1 Might. Your Kai'Sa, Survivor now has 5 Might.
   • The Kinkou Initiate ability resolves second: It checks the total Might of your other units. Since your Kai'Sa, Survivor now has 5 Might, the condition is met, and you draw a card.

Important Notes:

• Total Might: As confirmed in RiftJudge FAQ #9977, Kinkou Initiate's ability checks the total Might of all your other units on the board, not just a single unit.
• Timing: The check for "total Might 5 or more" happens on resolution, which allows you to boost your other units' Might to reach the requirement before the draw ability resolves.

This interpretation is based on the standard LIFO resolution of the chain and the rules regarding simultaneous triggers. No official FAQ exists for this specific combination of cards, but it follows the same logic as the interaction described in RiftJudge FAQ #9873.