You got some great points in the post!
I always thought that Hive as a whole as well as dapps/communities on here need a more stable plan how to advertise themselves other than word of mouth,sure that way is great also at times but we also needs ads on other sites,sure we are trying to get away from those big corp social media's and so on but one should never take an opportunity for granted by having ads running on those social media's (i ain't saying i will start paying for ads,but a pool to be used for that that the community can donate to/as well having a DHF proposal people can support) to be used for advertising on different sites would be great.
Also second thing that have been on my mind since i joined Hive is even though the crypto community as a whole could easily get into Hive because they know about keys and stuff...the mainstream social media users want it simple and a lot of people wouldn't even understand or even want to understand about keys and such and just look away because it's too difficult for them.
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The advertise issue is a key, is not necessary to promote on Google or twitter (twitter could work tough) but at least to promote in sites related to crypto. Also do some intranet advertise among community's and dapps could work. But there is when I realized that every community/dapp advertise only his own material.
Proposals like the carried by @ocd understand this dilema by trying to boost new communities. Don't know why they not boost games (with delegations) but boosting new communities helps a lot.
Also is very hard to be informed on new contests, a calendar would help a lot