Okay, Joe, take a deep breath and exhale slowly. You may be over-thinking this.
Of course, you take an hotel room with internet service, preferably free. Use a digital camera to take pix of receipts. Inser tthat SD card into laptop; upload pic of receipt; rimse and repeat. A few really hardened road warriors do take a scanner and a ton of other gear, but they may be on the road for 2-8 weeks at a stretch. That is NOT typical. However, a good GPS with updated maps and a recent version of MS Streets and Trips are essential!!
You will not need a printer. Most hotels will let you use their printer, in the privacy of an area dedicated to guest business needs. You can either use a data stick to take your document to their printer, or some have wireless remote printing to the business center computer. Or, you can just print out your instruction/surveys before you leave home. As a last resort, Staples or similar stores will print stuff for you.
Hiding things? Well, sort of. I try not to take my mouse pad with the obvious name and logo of an MSC. I take a small accordian file for paperwork. I use alligator clips to secure receipts or put then into envelopes. I take pix immediately of all receipts, just so they don't blow out of the car window (It happens.) I use a small digital voice recorder where it is legal to record interactions with hotel or airport employees. Otherwise, I get out of sight and write notes. When I leave my hotel room, I place the do not disturb sign. I do not hide or lock up my laptop, but I also do not leave it open and tuned to this site.
Now, many of us do like to take some comforts of home on the road. And, having enough "stuff" to make it seem sensible to need a bellman is an asset for hotel shops that include bell interactions. For many road trips, hotel shops or not, I take a favorite pillow, a cooler with re-freezable "ice" blocks, snacks, beverages, a few zip lock bags for leftover carryout food, emergency boots and coat (which may just stay in the car, of course) phone, laptop, power cords/charging cables for all electronics, wine, cork screw, a nice acrylic wine glass, lots of alligator clips, a good book, crossword puzzles, mouse and mouse pad. Don't forget a swim suit and some very casual clothes so you can chill when the chance occurs. For trips longer than a few days I also take some laundry detergent in those little blister packs (many good road hotels have laundry).
When you are doing a route, you can almost always negotiate due dates and times with your schedulers. Hotel internet speeds for uploading range from dismal to worse, for video and audio files (with a few exceptions that can be found in other threads or at VSN). Some hotel systems will simply fail. Your schedulers need to be ready and you will need to keep them informed while you are on the road. This is yet another reason to build rapport and trust with schedulers!!!
My advice is to start with baby steps by doing a route of only 1-2 nights. Then review what went right and what wrong and what was uncomfortable. The next short trip should be easier. No one just started shopping and zoomed straight to Road Warrior status.
Based in MD, near DC
Shopping from the Carolinas to New York
Have video cam; will travel
Poor customer service? Don't get mad; get video.