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RE: My initial STEEM purchase stopped at LTC and (wtf is whaleshares and beyond bitcoin?)
I would look into blocktrades.us
I found this review of the service, but it's 7 months old.
You may want to try several methods using only $100. Like send some through your market site, and send some through blocktrades.us and some throuth tradequik. See which method gives you the most STEEM.
I believe blocktrades.us is the quickest and easiest, but I don't know about the rate you'll get. One nice thing is you don't need an account on blocktrades to use it.
Waleshares and beyondbit are tokens for buying votes on steemit. They're not intended for investment, as far as I can tell.
Also your explanation on what whaleshare and beyond bit is helps simplify it. Blocktrades doesn't handle USD to STEEM. It handles open .usd which is still a form of crypto. I initially wanted direct fiat to usd such when you first purchased BTC.
I haven't found a good way to get USD into crypto. I'm stuck with coinbase's limits too. As someone else mentioned, localbitcoins is likely a good option, but I've been too scared to try it.
The blocktrades info that I posted is to help simplify the LTC (or BTC) -> STEEM conversion part of the process.