I'm with you am afraid - DS, now almost 9 months has never slept well in the evenings. I've tried every theory - over tired, under tired, too good naps, too little naps (our current issue) and nothing seems to make sense. He cluster fed in the evenings when very little and now, having resorted to co sleeping, he sleeps much better when I go to sleep. There are not many people it seems, that have this problem in the evenings, even if babies often do not sleep through the night yet. sometimes we can have 6 wake ups between going to sleep at 7ish and myself going to bed between 11-12. So no evening here either. Only rarely can I get him back to sleep without feeding.
Once I go to bed it's not too bad, comparatively, usually about 3 wake ups from midnight until 7.30-8am. Although I realise to some people that would be a lot!
My gP has prescribed liquid antihistamine to see if it an allergy giving him a nasal drip that wakes him up. Hasn't made much difference so far but we have been on holiday.
I intend to try some gentle sleep training soon and try to get him in the cot, with the theory that it might be because he can't self settle so wakes every cycle, but like you OP I don't Ike the thought of much crying.
So not much help for you except that you're not alone with this :)
I rarely have an evening to sit and relax and going out at night on my own is stressful as I know DS and DH will both be having a hard time without me there to settle him.
On the plus side DS seems very happy, healthy and his lack of sleep routine means we are flexible ourselves in terms of being out and about, visiting people and having holidays etc! Although I do worry about him not getting enough sleep as his naps are increasingly crap too, not for want of a lot of hard work on my behalf. When people say babies NEED x amount of sleep a day there seems to be something of a silent OR ELSE afterwards. I do worry about what that might be! Although like I said at the moment he seems very healthy and happy.
Maybe they'll just grow out of it...