MKA742 - just to answer a few of your questions:
Cheapest place would be the backpackers - there is no place to camp really, would be rather unsafe also.
There is no single bar where chiefpilots specifically hang out - this is not Maun, there are actually more places that people like to hang out, so they do not stick to one specific place. To give some of my personal advice: don't speak to any chief pilots in Windhoek - always talk to the boss directly.
The airport you are interested in, is the city airport Eros (FYWE) - you will be arriving at the international airport (FYWH) and there is nobody there and it is about 80kms out of town, so the first thing you will do is take a taxi into town for N$120 and take it from there.
Everyone is in their own buildings or hangars at Eros, exept Sefofane which are located in town.
There is no cheap connection from Windhoek to Maun - Air Namibia is the only one that used to do the route with the B190 - I don't know if they still do. Before you do that though, take a trip with Wild Dog/Crazy Kudu and view some of the country and while your on the trip check the guys in Swakopmund - if Windhoek doesn't happen, this might be your adress.
January is not the best time to go jobhunting in Windhoek so maybe hang onto that return ticket - but give it a try. It usally gets better from March to April.
I assume you come from the Netherlands - try to seperate yourself from others by offering a language bonus for all those Dutch tourists that you might be flying, if they take you - this can be a huge bonus to your advantage and show some general interest in Namibia. What a lot of guys don't realise, is that the flying job in Namibia is only a small aspect of the job and it is not only your pilot skills that they are looking for. You will spend a lot of time with the tourists and you will have to be a good communicator and do your best to give them a holiday of a lifetime - so that they want to come back. So start improving your knowledge of the country as best as you can. If you don't want to make the effort, you will be like most others coming there to get the job.
Good luck