What route would you go without breaking the bank? I am also thinking of purchasing the Westcott perfect pair kit.
Again, you either need/want ETTL & HSS, or you don't.
Personally, for speedlites, I have no use for ETTL & HSS for portrait and studio lighting. So I use manual flashes and simply control them and meter them myself. I prefer this.
I use the YN560-TX controller with a fleet of YN560 III's. Inexpensive. I buy my 560 III's used as often as possible (around $50 each time). I have 6 flashes. I often gang up speedlites in groups of 2 or 3. So this system is perfect for this. It's also a lot of light for a dime, with no frills, and less components (no transceivers, all built in, so less batteries too). A controller & 3 flashes is only going to cost around $200 roughly. For you, getting 560 IV's (the newest version), it will be closer to $250 for a 560TX controller and three of the 560IV flashes. That's still a great setup of light.
Alternatively, the YN685's do the same thing as above, but also have HSS & ETTL built in as options. They're twice the price, but three of those and both controllers will run you about $400. But it's an end-all-be-all system, you have all features possible, and they all have it. So it's a matter of need vs cost. I don't need ETTL for portrait work, ever. I control light. HSS can be useful, but personally, I don't fool with speedlite HSS, I find it's too weak for it's applications. When I need HSS, I use my portable 600ws strobe when I want HSS to beat down ambient light in blazing sun. So my speedlite fleet is all manual.
That Perfect Pair Kit is absurdly over-priced. I wouldn't get that.
For modifiers & stands, I would keep it very simple. You wanted portable as you said. So let's keep it portable (light weight) while having good surface area. Here's some suggestions:
Adorama Boom ($80) - One of these, for suspended, or any kind of interesting placement for key light(s). This thing can handle several speedlites ganged up and suspended out. Weight & stake it down when you're outside.
Neewer 9" standard Stands ($27 for both) - Simple stands, they will hold stuff fine, just stake/weight them down.
S-bracket Mount ($18) - Get one for each light you plan to use. These are far better than cheap coldshoe mounts and if it takes a dive, much more likely to survive (the flash). These have the umbrella mount & a bowen's mount, so it pulls double duty and keeps your flash closer to the center of the modifier (this can be important).
Double Hotshoe ($19) - I use one of these when I want to gang up two lights together as one source. This is important if you shoot in brighter light or use larger modifiers (like 48~60").
Godox 31" Brolly Box ($20) - Great modifier as a hair light, rim light, or key light for a single subject, super portable as an "umbrella" but becomes a big softbox. Get one or two!
Godox 47" Brolly Box ($30) - Awesome key light modifier for one or two subjects. Big yet portable, again, it's an "umbrella" but becomes a big sofbox. When I use this, I often use two speedlites ganged up together so I can get more spread, more output, and more distance with it for my subject(s).
1/4 CTO Sheets ($12) - One will give you tons of enough of this. These are for blending your flash temps to warmer temps to better blend into ambient outdoor light in the evening. Flash temp is fairly cool temp, it's very close to day light white balance. But in the evening, the temps of light in ambient light warm up, so your flash looks cold and sterile compared to the environment. These gels are what you use to warm up the flash to blend it into warmer ambient light to look more natural. I use velcro tape to attach mine to my flashes, so they come on and off super easy. I cut them myself from these big sheets. Plenty to go around so if you lose one or tear one up, you make another with tons to spare. I'd call this mandatory if you want to strobe in ambient outdoor light in the evening.
Softlighter II (60") ($115) - Huge 60" modifier, excellent quality. It's probably too big for even two speedlites unless you're in a studio (then it will work fine). Outdoors, I would use a strobe with much more output. But, just wanted to throw this in the mix to give you an idea of what it would take to light up a small group, or a couple, with some distance --assuming you have the output for it (ie, strobe). This can however work with speedlites at close distance (great suspended over head on boom) with two or three speedlites ganged up in lower light (early morning and late evening).
Here's the Stakes & Bungees I use (cheap!):
9" Nylon Stakes ($15 for 6 of them) - This is enough for two lights, but I suggest enough for 4 total bungees (8) so get two.
24" Flat Bungees ($7 for 2) - Get 4 total, two per light basically.
Batteries:
Eneloop AA's (4x + charger, $16) - They hold charges awesome. Charge them all up the night before. Shoot all day.
Eneloop AA's (12x, $30)
Personally when shooting outside, I only use two light sources. Sometimes only one! I use natural ambient light in the mix. I generally use a big modifier as my key light, or as fill, depending on my look I want, on a big heavy boom stand. I let the sun or ambient light be my rim or hair light if it is falling nicely. Otherwise, I use a 2nd light source as a hair or rim light, just out of frame, I generally use a smaller modifier (sometimes no modifier at all, and just take the power down so it's a stop under my key exposure). I stake & bungee my stands down. I shoot in full wind in Florida at the coast and in fields no problem. But I have to stake down, I can't just use weights, I always stake down. If I can't stake it down, I can't trust it to stand up. My simple rule of thumb so I don't bust stuff.
So, you could do this:
Yongnuo YN560-TX x 1 ($45)
Yongnuo 560IV x 3 ($210)
Adorama Boom Stand x 1($80)
Neewer Stands x 1 ($27)
Double Shoe Mount x 1 ($20)
S-Bracket Mount x 2 ($36)
47" Brolly Box x 1 ($30)
31" Brolly Box x 1 ($20)
Gel CTO Sheet x 1, and get velcro tape ($20 with the velcro)
Stakes & Bugnees (8 stakes & 4 bungees linked above) ($45)
Eneloop AA batteries (4 per flash, 2 for TX, 14 total, get the above linked and you have 16 and a charger) ($45)
$580!
But that's a total, complete package, with all bells & whistles. Everyone always thinks they'll get a a few lights and keep budget down. But you have to have the modifiers, stands, and you need portability and security while doing it and that adds to cost to be able to make it all work by yourself in windy locations. Plus you just need a lot of little accessories that you don't think about until you actually start shooting and using it and realize you need stuff. The above linked is literally everything you'd need, no frill, literally all pretty much staples and workhorse material. That whole setup cost a little more than a single 600Ws strobe, to put this in perspective of how costly lighting can be.
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Stake & bungee, I use inexpensive 9" nylon stakes that I drive into the ground with my shoe. I then use 24" bungees to brace down my stands with lights+modifier. I do doubles if it's big modifiers and/or heavy on top, or when I'm using the boom at full extension, etc. I consider this mandatory. If I cannot bungee & stake into the ground, I find another spot. Weights don't work in the wind in my experience, that's for studio. I need bullet proof because I work alone with no assistant to hold things in wind. So I use this method and it's not fallen over yet in full wind.
IMG_8962 by Martin Wise, on FlickrExample of two lights ganged up, with CTO gels velcro-taped on, ready for the modifier:
IMG_6076 by Martin Wise, on FlickrExample of two lights, suspended over-head at an angle with a 43" umbrella in evening ambient light (still bright!), with the Boom stand, a counter weight (bag of waters), and bungees and stakes into the ground. Holds it even extended out like that no problem. Sun is camera right, that's rim/hair naturally. Notice there's a simple stand with a bair flash with gel in the background in front of that unsightly lawnmower, that's a hair/rim light too. Both are out of frame:
IMG_9707 by Martin Wise, on FlickrHere's the kind of light I was able to get out of 3 speedlites in evening (bright though) light (with 1/4th CTO gels to blend flash temp into ambient temp so the white balance is similar on both). Notice the over-exposed right side rim is actually the sun, it was that bright out. My flashes were actually fill lights in this case. This is why I had to use two speedlites ganged up, to get the output needed to combat that bright sun for exposure. I nailed exposure without wasting a lot of time, by using a light meter to test my flashes and measured/metered the light output from them at the pumpkins to be very close to my aperture (F2.8). I adjusted the flashes output (both of the key flashes) remotely with the TX560 controller until I got F2.8 output on my meter. Done. I placed the baby and bam, no wasted time, got exposure right. Also note, because I use the TX560 groups, I was able to put both of those key flashes into a single group, so when I change their settings, both get changed together, even faster and even more simple. By the way, I put big white letter stickers on all my 560 III's (A, B, C, etc) to identify them so I can quickly change any light I want remotely with my controller as they correspond to the controller's group names (which are A, B, C... etc).
IMG_6096 by Martin Wise, on FlickrLastly, I will note, I used to never use light meters and I just chimped and changed things. Now, I use a light meter, and I absolutely adore it. It makes portrait lighting outdoor so much easier & faster. And since I can control the power of my flashes remotely from my TX560, it just makes it even faster. I meter, trip my flashes (without even taking an image with the camera), change power to what I need, or adjust camera settings to what I need, test again with meter. Done. Start the shoot. They run $100~250 for entry and mid-tier ones. I highly recommend a simple Sekonic light meter. Speeds things up and you get the right exposure (so you're not guessing while looking at an LCD in the sun).
Very best,
