I've been tagged by shr.ink, so I will try to share my experience as best I can. For reference, you can find all of my domains listed over at DadDomains.com and can view my NamePros profile to find the sales threads I have over here.
Right off the bat, I don't have an answer to the "Is it worth it?" question.
For me, as someone who lives in Eastern Europe and has zero debt, it's fine. It's a relatively stress-free way to make money, even if books won't be written about this model. It is what it is and for me, it's okay. I work super hard each day so as to find good domains and I sell at a margin small enough to make it worth it for buyers, while still enabling me to put food on the table.
If you live in urban areas of the US, forget about it
Same if you live in Switzerland, Australia, Canada, Japan or any other country where the proverbial system can offer good employment opportunities.
So that covers the nuances of the "is it worth it?" question.
Moving on to the how, here's the breakdown in my case of where the $ comes from:
1) end user sales in the low to mid $x,xxx zone, which occur even for someone like me with probably the highest str in the business. I sold my previous portfolio which consisted of a low x,xxx number of domains completely and will probably sell the DadDomains.com one as well within the next few months. 100% str if you want to go there, lol. But even so, until those sales materialize, there will be periods when you sit on ample inventories (over 3,000 domains in the DadDomains portfolio at the moment of writing) and end user sales will occur, even if rarely
2) low-volume reseller sales at higher per-domain values. I frequently wholesale domains close to the $100 zone but obviously cannot move the volumes I need at these prices, but still it's a revenue source
3) medium-volume sales in the mid $xx zone, a very reliable stream of income at such prices from domainers who know what's missing in their portfolio and want to cherry pick. I have buyers who come to me whenever they get an end user sale and buy more, consistently
4) huge sales at lower prices, with my "record" for a single sale being 800 domains in one day to the same buyer, in just one deal
Finally, to answer the "how to sell" question, I will say very clearly that given how inefficient and illiquid the domain market is (which is both a blessing and a curse), it very frequently happens that a certain sales venue underperforms for long periods of time and then does very very well, restoring the balance. So the key is not trying to find that one perfect platform (it doesn't exist) but rather having a consistent presence everywhere.
Where, specifically:
1) Forums, like NamePros
2) Your own repeat buyers with whom you establish relationships
3) Paid ads every now and then
4) Developer communities, where you sell at prices between wholesale and resale, have had sales this way but it's hit or miss
5) Special events and auctions
6) Outbounding, something I have done in the distant past but no longer do given my large portfolio sizes. But keeping an open mind for when our AI overlords make it possible to outbound at scale through agents and what not
Hope I didn't miss anything.
Did my best to offer a pragmatic, realistic perspective.
For me, it's a way of making money by working hard BUT in a relatively stress-free manner, which I appreciate. Not saying this is the best way to do it, it's probably not for most people, but it's the best solution for me at this particular stage in my life. Good luck and have a great weekend! If you want to buy names on the cheap, PM me, as I have two land deals closing in January and am more motivated than usual to move inventory at scale. Maybe even the entire portfolio before the year is over, why not?