First of all,
not Cryptostocks, which has already been completely hacked on more than one occasion , and operator already defrauding user for long time, just the latest scammy antics are here.:
https://bitcointalk.org/index.php?topic=569037.new#newto use cryptostocks will be like keeping your money on mtgox or inputs, it's not responsible as asset issuer and not fair to a shareholder to ignore such warning signs. balances are at risk.
I don't think you'll run into huge problems with Havelock in near future although sec for sure will be interested in getting their mitts on operators. but they are smooth and reliable up until now and keep low profile, because they already know the risks. biggest issue there right now is expensive hosting fees which will eat into your profits.
Direct is good, although trading will be a headache(you will be mostly stuck with holding), Ken will perhaps need full-time staff member to update spreadsheets and do correct due-diligence on any share transfer or modification requests, there will be some fraud attempts.
Colored coins is OK, but mostly a pipe dream, closest is the prism implementation, The best of both worlds, CounterParty is ready and active right now..
https://counterwallet.co/It will cost ken just shy of 70 cents to list his asset, there is not a risk of a random exchange 'hot/cold wallet breach' no risk of exchange operator playing fractional reserve on your balances.
Dividends in BTC are sent DIRECTLY to shareholders. (NO middle men. & no requirement of XCP tokens) Shareholders are free to trade their shares at any time.