Disclaimer: Chaddy - Stay out…this is for Sal's eyes only ;)
The level of friendship with these people is up to you. In any case the relationship is a positive one, so put some thought into how that may have happened.
1. Magravi Family: Operate and own Risa's Place (a tavern frequented by locals, such as yourself…and free from Sczarni as far as you know). Old Risa (who is half-blind and is able to wield magic) has recently turned over the running of the place to her 3 children: Besk, Lanalee & Vodger. (An obvious conection is you hangout here and protect them, or have worked for your keep. I might have to detail these 3 a little more now ;)).
2. Maester Grump: An aging farmer that runs a farm south of Sandpoint (b/w the Ashen Rise and Whisperwood) with his small family. (Another potential employer when funds were low).
3. Vorah Ween: Wife of Bilivar the Wainwright; Their daughter drowned in the Millpond last year and Vorah is overly protective of her other 2 children; You have been noticing Bilivar spending more time frequenting taverns of late. (Heaps of ideas here: perhaps you tried to save their drowning daughter, maybe you did save one of the other two children. You could simply be sympathetic to Vorah, having noticed her husband at Risa's Place a lot lately).
4. Gaven Deverin: Aging knight turned brewer that owns and runs Two Knight Brewery; Unfortunately there is only one knight now - Gaven's brother Wade was one of Chopper's victims; Cousin to Mayor Kendra; Clothing always worn and torn and lately is getting his directions wrong. Perhaps you once worked here too. (Maybe you just liked the place - being a brewery and all. In any case, maybe you are concerned with Gaven as he becomes more disheveled).
5. Arkin Ironshanks: A likeable dwarf cleric that arrived in town around 2 years ago and helped to keep you out of trouble - even getting you a labourer's job helping to build the cathedral.
6. Grontwin Glimmerstone: A roguish dwarf that arrived several years ago and quickly joined your ragtag band of thugs; In fact he has been the one constant and along with Arkin you have developed quite a friendship; Likes to cause trouble, but everyone seems to forgive him or laugh it off. You have recently helped him with a scam to lure his 'do-gooder', studious cousin to Sandpoint 'so he can have some fun in his life'. You are hoping this Byrak will arrive in time for the Swallowtail Festival.