If you're really in a pickle where you're worried about your security for communications and intend to communicate in short bursts or time intervals, consider the following:
Get a "burner" laptop, preferably a second hand cash purchase
Buy gift cards with cash for a local electronics store like Frys
Buy a replacement NIC and HDD at another Frys with the gift cards
Install, use TAILS for tests
Only transfer materials or information to your laptop via media like USB
Be aware that photos may carry EXIF or location data, and Microsoft files and such may carry licensing info, user IDs, etc.
Know your media content well and exactly what is being transferred
Get a VPN at a provider that takes gift cards in payment (some do)
Buy gift cards with cash at 3rd party locations like Supermarkets -- you can many like Target, Amazon cards, etc - whatever your VPN provider takes
Buy your VPN service with that
DO NOT log into your VPN service or test from home, work, or a known location
Seriously, never do this. If you've logged into your VPN from near your home, start over
They busted the Silk Road guy by being a dumbass and using coffee shops routinely within blocks of his condo to work out of
Test from the library, or other public venues
Research and become aware of where you have free public wifi that is unlikely to be policed back to you specifically
Assume cameras are everywhere
Assume every angle is camera covered, including outdoors
If you're lucky to live in a city with decent municipal wifi, like say San Jose, you can sit anywhere -- inside a foyer, for example, and they will be hard pressed to visually tie you to your actions
Always use your system in a crowd if you can or from a private venue
Don't just fire up your laptop at 1pm in a visible spot where you're the only person doing that sort of thing
Do things at peak activity times -- 730am to 830am, 12pm-1pm, when people are coming and going
After work rush isn't as good -- people won't loiter and linger in lines and crowds, they're leaving with a purpose
Use TAILs and this VPN only from that sort of public venue, preferably where many people do such things, like coffee shops
Have everything you plan to do laid out ahead of time - maximize planning
Log in, get online, do what you're doing cleanly and get out in a calm and reasonable manner
Starbucks hypothetical: buy your coffee and cookie with cash. Is your name Bob? Tell them your name is Steve.
Drink your coffee. Get online. Eat your cookie. Do your online business. Look at the weather online. Smile at people if they smile at you if that fits your culture. Be normal. Be average.
Drop or raise the pitch of your voice.
Fuck up or fix your posture a TINY BIT; if you're ex military don't Quasimodo that shit
Don't limp or anything that stands out: you are not Kaiser Sose
A good example -- Christopher Reeve changing from Superman to Clark and back again, on this link. Don't watch this FROM YOUR OWN COMPUTER or whatever, duh: https://www.youtube.com/watch?v=BIaF0QKtY0c
Make a list of all such locations available and accessible to you - as far as 20 miles away perhaps
Number the list
Get some decent free app that does random number generation -- dice rollers, generate random integers
Randomly choose a location
Assign a random interval of 1-10 days before you will use the system again if possible
Most retail type outlets will rarely keep video more than a few days
If you're dealing with really secure leaked stuff, expand your radius to 50 to 100 miles
If you can identify at least 20 safe locations -- and by ID I mean GO to them, do not Yelp, walk in, eat lunch, get coffee, whatever -- all CASH, each time! -- that's good.
Always change your order, never customize or substitute your order, don't give them any shit about vegan this or gluten that. Order a boring ass latte or the lunch special. The next time do a regular chai or the fish
Assuming you will only do this every 1-10 days and you have 20 locations, you may not be back to a given spot for weeks or even months
I challenge the average barista or waiter to remember a given person who shows up 1-4 times per year in their place, especially if the person changes their posture or outfit routinely or even their persona a tiny bit
Buy a lot of common hats and several jackets and hoodies that don't stand out--no team stuff, sports teams, etc.
If you're going to use a Starbucks on Wall Street at 745am wear a suit, look sharp and crisp. Fit in. Don't go in with a black hoodie.
If you're going to use a Starbucks on a major college campus hub at 12pm between classes don't wear a suit, dress like the kids if you're that age or a teacher if you're that age
Know your environment, look and be as statistically average as you possibly can
Use events for timing: is there a viable communications location at or near a concert hall or stadium? A bar next to an NFL stadium on game day? Crowds and anonymity in numbers are your friend
Several pairs of sunglasses or eyelasses with plain glass lens
Be ten different Clark Kents. Choose them randomly too
If you rock facial hair, lose it - still far more uncommon than clean shaven and it's a marker
DO THIS ALL AT LEAST CORRECTLY A HALF DOZEN TIMES BEFORE YOU DO YOUR STUFF THAT IS IMPORTANT. Dry runs. Test. Did you sweat? Don't sweat next time. Did you fuck up? Don't fuck up next time. Until you can do it six times or more in a row without fucking up, don't do your Thing.
Also: anything that YOU KEEP AT HOME should be deep inside of multiple layers of encryption. Example, TrueCrypt and alternatives. Hidden volumes. Say you have 1 GB of data to keep secret at home during all this. Use a Mac at home as your main system? Encrypt Mac with FileVault, do NOT do the "keep key with Apple" option, and inside of that put several 10 gig encrypted volumes. Inside each put a 7 gig encrypted volume, then 4, 3, whatever until you're 1GB of real data - like Russian nesting dolls. Each with a unique key and password.
Think of your entire security model as Russian nesting dolls: the more layers you do right the safer you are. The more layers you fuck up the more you're caught, but remember that one fuck up in the wrong place will end you.
May the force be with you