Choices for leaving cats while on vacation

Okay, here's the story:
Going on vacation to see family for seven days in August.
One stray/feral that has just recently warmed up to us after eight months
A friend that offered to come before and after to work to look after the darlings.
We usually take the other two cats to a kennel. Don't ask, it works.
I don't like having a good friend, animal lover extraordinaire that she is, cleaning three litter boxes and the odd hairball or two for three cats.
Do we take the other two to the kennel and leave Pru behind? Being out of her environment with us would really set her back, I don't even like to think of her in a noisy place, noises in our house scare her, but having a stranger in the house will not be good either. The other two are fine going to the kennel, they've gone there for the past 5 years, it's where we adopted Sam.
So the choices are:
1. Take all three to the kennel.
2. Take two, leave one behind.
3. Accept the generous offer and keep all three home.

If you have the option of keeping your babies at home, I'd suggest doing so. Why take them out of their environment if you don't have to. Wow, lucky you, how nice to have friends like that! In regards to your recently warmed-up feral, perhaps you could ask your friend to spend some time at your house before you go on vacation. That way the feral (hopefully) will get to know the person's voice and won't be so frightened when you're away. You may also want this person to house sit for you so there is a bit more of a routine for your babies (versus someone coming in and out of the house).

My neighbor and I exchange cat-sitting services for each other. We each leave our cats at home and the other one goes over to the apartmetn to tend to the other's kitties. We are happy, and the cats are happy too.

Keep all three at home.

Your concern seems to primarily be not setting back the progress of the new one, and keeping all three at home is the closest thing to the status quo possible.

I agree leaving all three at home is best. I don't like to inconvenience anyone and I have to get over that. Pru has really found a spot in our hearts. She needs more TLC than the other two sweeties at this point.
It's my friend or the cats. The cats win.
Oh they all win, my friend loves animals and wouldn't offer unless she wanted to. I just have to accept help when it is offered.

I also agree with leaving all three at home. If you put just the two in the kennel, Pru would wonder where her pals went. We have a friend come here to feed Abby when we go away. Abby pulls out her fur when she gets nervous. Normally when we come back from a trip, we are greeted by big blobs of fur, and bare patches on Abby. The last weekend we went away, I plugged in a Feliway diffuser. When we got back, Abby hadn't pulled any fur!! Maybe this is an option to make Pru feel more relaxed while you are away? We are also going away for a week in August, and I already have the Feliway ready.

Great idea Karen, I hadn't thought about Feliway.
I can picture Abby and her hair blobs all too well!

It's really not a pretty sight! I am hoping we have good results again It's amazing that a cat that doesn't show affection easily is so distraught when you leave, and so affectionate when you return. The first time we went away, after only having her a few months, our thought was "Awww, you really do love us"