I find my best bet is to keep it local. I have sold very little on ebay and I find it to be a pain-ebay fees, shipping, trying to work the ad just right to make sure it gets looked at...I am not a marketing genius here, I don't wanna compete with stores and people who do this for a living. I just wanna dump some crap from my house.
So, craigslist, garage sales and consignment shops are how I sell, when I want to sell.
Garage sales-now is the time for end of the season sales, so people are out lokoing for them. And you can advertise on craigslist for free for a sale, and that is how a LOT of folks find them. I had one the first weekend in August. It was super tiny...but then I live in a neighborhood that has two neighborhood sales a year, so I just joined in that. That does make it easier. But seriously, all I had was a coffee table, about 15 clothing items from my teen daughter, a small crafty looking end table, a microwave, an ugly green chair, some books, a small handful of other odds and ends and then two cars. We actually SOLD one of the cars and then $30 worth of the the other stuff too! I threw it together the night before and listed it on CL...and most of the people that stopped by actually said they saw my ad on CL and that's what brought them out. And when you add to the considerations that I was 32 wks pg, it was August and my only helper was my disabled MIL, I was impressed we sold ANYTHING. It sounds to me like you have more than I did to sell, I am betting a garage sale would help you even more. I actually even held a garage sale in NOVEMBER last year, and made like $75, which isn't a lot but then again, it was NOVEMBER, it was like 40* out and so not garage sale season.
For stuff that doesn't go well in a sale, or if I don't feel like putting a sale together, Craigslist is the way to go. We sold a laptop on Craigslist last week, I had it sold within 2 hours of listing. The keys I find with CL-keep re-upping your ad...people look at the stuff on the first page or two. Especially in a busy area like babies and kids, it can sometimes be tough get the ad noticed. You can delete and repost an ad like every 48 hours. Also, the lower you price it, the faster it will go, which should be a duh moment but it's true. At the same time...ALWAYS price higher than the absolute minimum that you will take and be ready to negotiate. Everyone wants to negotiate. As far as pick ups...most folks, I find do like to meet in a public place. For some stuff-couches, cars etc, that's just not possible, but you know I haven't met anyone creepy or anything either. I think the safety factor is really no different than freecycle or a garage sale or having your name and address in the phone book. So often, I don't even meet someone somewhere unless asked.
As far as when I give up on selling and just dump it...that depends on why I am getting rid of it. If my primary goal is "get it out of the house" then it gets a shot at the garage sale, if I am doing that, or a week or so on CL (with regular re-ups) then it goes to goodwill, or the trash. If my primary goal is "we need the money" and I have the room to store it, I just keep it around till it sells. This goes for things of all values. We have donated a car to Goodwill before, because it's sitting in the driveway was more in the way than us needing the money.