I’ve never printed out a map, so I can’t help with questions 2 and 3, but I can offer some thoughts on 1 and 4 based on what I’ve done at home with the OOB Global 1940 map. You can see pictures of my particular setup in the first post of this thread: http://www.axisandallies.org/forums/index.php?topic=20658.0
In terms of printout size, you may want to “make the map fit your space” rather than the other way around. Choose the room in which you’ll be playing and make some measurements to decide how much space you want to allocate to the map table, to space for the players to stand (and/or sit) around the table, to playing aids like dedicated dice-rolling areas, to free surfaces on which trays of sculpts and chips and battle boards and other supplies can be kept, and so forth. (My table has a central map portion and two “wings” for use as all-purpose working surfaces.) Also plan for an area in the room where drinks and snacks can be kept – but this should be on a separate table located well away from your map table because it’s no fun to accidentally tip over a beer and have it wash away your armies and stain your map.
Once you’ve worked out your room parameters, start looking for a suitably sized table (or tables) that will fit the space you’ve identified. Your choice would be dictated in part on whether you want your setup to be permanent or not. If you have a room that you can dedicate full-time to wargaming, and if you don’t anticipate moving from your residence anytime soon (if ever), you can go for a large and solid table. If however you want (or need) to dismantle your setup from time to time, then a modular approach is better; in that case, you might buy several identical modestly-priced card tables with folding legs and set them up in a row (which is what I did). If you use that approach, you may want to put something large and rigid over the tables like a sheet of plywood to provide a smooth and level surface on which the game map can rest (which is especially important if the map is made of paper or vinyl rather than stiff cardboard).
Once you’ve got those infrastructure details worked out, you can then decide how large a map would be practical to print out. The priorities to keep in mind are to make sure that your table fully supports the entire map surface (the map shouldn’t dribble over the edges) and to make sure the players have ample room to move around the map while playing.
Regarding the plexiglass top, I’m quite happy with mine. It protects the game map from damage (scratches, spills, etc.) and it covers the fold creases in the OOB map boards to provide a smooth playing surface. Custom-printed maps don’t have fold creases, of course, but they do tend to curl up at the edges – so a plexiglass sheet helps to hold them down.
The material I used for my table is something called non-glare Acrylite P-99, originally sized by the manufacturer at 48" x 96" x 1/16" thickness. The local plastics company from which I bought it cut the sheet to the size I wanted, which is 36" x 96", so they just had to cut a slice from the width because the length was already correct. They then shipped it to me by delivery truck, rolled up into a tube about two feet in diameter as I recall (the rolling made possible by the fact that the plastic was just 1/16" thick). To give you a rough cost estimate, the price (in Canadian dollars) was $60 for the plastic itself, plus $10 for the cutting, plus $30 for delivery, plus another $15 or so for sales tax.
One bonus of having a plexiglass cover sheet is that it lets you customize the map to create special start-up variations (for instance a 1939 map configuration as opposed to a 1940 map configuration). You remove the plexiglass, put roundels of the appropriate type on the appropriate countries to reflect the political situation as it existed at such-and-such a date, then put the plexiglass back on the map. The map customizations are therefore under the plexiglass playing surface rather than above it, so there’s no confusion created between the roundels which are added during the game as the result of play and the ones that were put under the plexiglass to create the custom setup.