I'm a day behind in my #charactercreationchallenge. I'll have to catch up and skimp on my goal to have a useful image in each post.
In many of my campaigns, I use Assassins as soldiers. The reason for this is that assassins have valuable military skills for recon. While OSE doesn't specifically list spying as one of their abilities, their skill set supports it.
Meet Ormonde, a nicely named soldier-assassin.
Level 3 Assassin
Armour Class 5  (leather)
Hit Points 11
1 × crossbow (1d6)
1 x sling (1d6)
1 x short sword (1d6)
THAC0 19 
Movement Rate 90' (30')
Saves D13 W14 P13 B16 S15
STR 9 INT 13 WIS 12
DEX 17 CON 12 CHA 16
Items: Beastiary, country map, journal, papyrus, ink, 3 quills, knife, map case, lamp, oil flasks x3, sarcina, bed roll, trinket bag, 5 days of rations, 24 bolts, 2 potions of healing, 1 potion of giant strength, 2 potions of diminution, 6 potion vials of rum (non-magical), a small net bag, 100 gold pieces.
Ormonde is a veteran of many campaigns but has never progressed in the ranks. That has not held him back, he loves army life. Very often he is paired with a new lieutenant or unit of green troops. He has a special ability to teach the troops to campaign. He had a very hard time as a recruit due to his lack of strength and constitution. Often mocked, he was able to turn this around by putting his other skills to use. He was a master of collecting gossip and scuttlebutt, which he offered to his superiors and peers usually for a price but sometimes for free.
When things got rough, he can calm and soothe the troops. Many nights around the campfire, he would pen letters home for the new recruits or tell stories of fantastic (and funny) beasts. Ormonde has a funny map that doesn't seem to be useful for anything but telling tall tales. He has a trinket bag full of lucky charms, orisons of hope, and boozy potions of courage. Most of his "rations" fall under the category of welcome and surprising treats like dates and other dried fruits. Items that can be soaked in booze or poison or nothing at all.
Everything about him screams Bard, except for the whispers of things that happen in the dark. Ormonde uses his other abilities to make dangerous and foolish people disappear. He will do anything to keep his warband safe.
He is often elected or volun-told to travel with rookie troops and smooth out any mistakes or poor choices by the officers or the troops, one way or another. These special assignments require payment in gold to ensure what is desired by the officer or peer happens. Much to his credit, the vast majority of newbies return home with more skill and respect for the institution of soldiering than those who don't return. He is known and highly valued by a select number of veterans and officers in the army.
He is a savvy assassin. His sling remains hidden until needed either as intended or as a garrot. Ormonde will lend his crossbow out for hunting and take the time to teach how to ambush prey. He is a terrifyingly good shot, which is often more the point than hunting.
Ormonde is also careful to explain his potions to his peers, so as not to be mistaken for a poisoner. Many times he uses his potions on others in creative ways. Usually, the drinker is willing in the case of healing. On other occasions, he will dose someone with a potion of diminution before putting them in a net bag until they learn some important facet of soldiering or command. Other times, he will drink the potion himself to gain access to places he normally couldn't reach.
There is one famous tale about Ormonde which is usually told around the campfire. Ormonde and three young soldiers were cornered and almost captured behind enemy lines. He dressed in a dirty sack and gave his charges the Diminution potions before placing them in another dirty sack. He brazenly walked through several enemy checkpoints, offering to sell his bag of chickens to various officers and sergeants. He was kicked, knocked down, and punched so many times, it took him a month to look and walk like himself again, but he and his men escaped. Those three men are generals now, but cluck when he calls them "his chickens".