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Wouldn't surprise me if something can be found over at www.matrixgames.com
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Narakir: You could also give operation flashpoint a try, there's a whole guerrilla expansion for it.
That one stood out to me, too. Not sure if it's quite the game wanted, since some of those 5 listed elements are more within the backstory but not necessarily in the gameplay.

But Operation: Flashpoint is worth owning anyway, even if it doesn't completely fit the bill. Enormous library of mods for that game, too, so maybe someone has created a campaign that matches.
Donkey Kong

Oh wait, that's a gorilla warfare game.
Star Wars : Rebellion comes to mind, at least if you play the rebels at harder difficulty settings (at lower settings, the rebel fleet has got enough teeth to wage a conventional war early on)

The game is asymetric : The Empire has more powerful units (a Star Destroyer squadron can wipe out the entire rebel fleet if the Alliance does not flee most early battles), very good officers, good but expensive troopers, and a strong position in the rich core sectors. But they fight from a fixed position (they are forced to defend the capital at all costs), their best ships and soldiers are expensive and long to produce, and they have trouble garrisoning every conquered planets.

The Alliance has a good starting (and hidden) position in the poor, undevelopped outer rim, their heroes are mostly spies, commandos and diplomats, they have efficient and inexpensive fighters (and the fact that their fighters have hyperspace means they deploy them very quickly while the imperial fighters are still launching), and their HQ is mobile, meaning they can fight from hidden positions and escape imperial raids.

*There is no fixed front (sectors can have planets from both sides)
*covert ops (sabotage enemy installations, murder/abduct leaders, incite riots and rebellions on enemy-held planets, destroy planetary defenses before an assault...) is an important part of the game,
*information is key (if you want to strike an enemy target - fleet, officer, troops- you need to know where it will be, and what are the system's defenses. On the other hand, you want to know where the enemy fleet will strike to evacuate your assets before the imperial forces get you into a desperate "battle of Hoth" situation, or if Vader is currezntly infiltrating one of your systems),
*hyperspace jumps means you can't corner an enemy to a decisive battle in the early game but you can force them to flee to a faraway place where they won't be of any use for quite some time.
*And raids allow you to whittle down the opposition and fade. Especially if you play the rebels, who bases their battle strategy on cheap but efficient fighters, but very unimpressive capital ships. The rebels can afford to lose fighters in droves, while an imperial destroyer is a formidable opponent, but very vulnerable when its Tie squadrons have been whittled down, and its loss is crippling

Of course, playing Empire on easier settings means you'll be in a more conventional "find and crush the rebel scum" scenario, but there is still plenty of guerilla opportunities to be had when transports full of spies and special operatives enter in a rebel sector.
Post edited February 01, 2017 by Kardwill
Not sure it is the type of game you are after but there are most of the elements you are looking for in ArmA: Resistance.

It is a tactical first person shooter sadly no longer available on Gog.

I personally found the resistance campaign to be the best- hit and run, ambushes, stealing equipment etc..But it is a hard game to play as you do need to control at squad level and may be tough to get into if you don't like the genre.

If you are interested but not sure you could check out some videos first.
This might sound silly at first, but I think the game that fits your criteria best might be
Gangsters: Organized crime. Here's why:

1. You control only a handful of men, most are usually poorly armed (expense!) and have poor training
2. Territory shifts constantly, only your hidden office (HQ) stays the same, mostly
3. Oh my yes. If you out yourself as a mob member, police, FBI and rivals will be on you like flies
4. Definitely. Recon is paramount. You don't know about anything in your surroundings if your men haven't identified it as such and such. And hit and run tactics must be the basis of your modus operandi.
5. Your goal is to wither the enemy down to as few men as possible, hit their recruiting and extorting people, raid their businesses, expose their shady operations to the cops etc...

Try it out, you'd be amazed how dead on the game feels like having your own guerilla force.

edit: link fail
Post edited February 01, 2017 by Titanium
Vietcong, perhaps?

[url=https://en.wikipedia.org/wiki/Vietcong_(video_game]https://en.wikipedia.org/wiki/Vietcong_(video_game[/url])
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KasperHviid: The first thing that popped into my mind was AI WAR: FLEET COMMAND.
Oh, good point. It's not the game that would have sprung to mind immediately for me due to its aesthetics, but your fighting style is a bit similar to that of guerrilla warfare.

Vietnam '65 has you fight against a guerrilla force as the US. You're not the one actively conducting guerrilla warfare, but you need to fight it through the means that a conventional army has.
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AFnord: Vietnam '65 has you fight against a guerrilla force as the US. You're not the one actively conducting guerrilla warfare, but you need to fight it through the means that a conventional army has.
Thanks for the recommendation. I started playing Vietnam '65 and it is really great. As you said, the player is not the one conducting a guerrilla war, however, combating against one leads to a very interesting and unique gameplay experience.

There are no front-lines, the win objective is basically "hold on as long as possible without being unpopular with the civilians", and the enemies keep popping out of nowhere.

The mechanics are rather simplistic, and I'm not sure how long it will keep me interested for, but for the moment I'm really, really enjoying it.