TBH you haven't, you have made some vague generalisations about what you think, but have failed to actually quote the relevant act(s) or even give any indication that you have read them.
**TLDR - Nothing about Hitting it Big (or similar sites) contravenes any (current) Isle of Man laws as long as they are not operated from this jurisdiction.
FYI (in case you are not aware of it)
The legal definition of a lottery (Lexis Nexis)
....Lotteries involve the distribution of prizes by chance to participants who have made a monetary contribution ...
In the UK THE GAMBLING ACT 2005 has provision of these 'skill' games that qualifies them as a lottery. (see Section 14.5)
A process which requires persons to exercise skill or judgment or to display knowledge shall be treated for the purposes of this section as relying wholly on chance if—
(a)the requirement cannot reasonably be expected to prevent a significant proportion of persons who participate in the arrangement of which the process forms part from receiving a prize, and
(b)the requirement cannot reasonably be expected to prevent a significant proportion of persons who wish to participate in that arrangement from doing so.
In the Isle of Man GAMING BETTING AND LOTTERIES ACT 1988 is concerned with and only with gaming, betting and lotteries conducted on the IOM and is only enforceable against those on Island and is concerned with those actions that require actual gaming (rather than online.)
In the IOM we have not adopted the variation of these 'skill' games that would have them seen as a lottery, The IOM can not view this as a lottery because there is a question to answer, regardless of how simple that question is.
The closest that you will find under this legislation is 29.1.e, but this can not me applied to online games.
Online gaming is covered by ONLINE GAMBLING REGULATION ACT 2001 (more commonly known as OGRA)
OGRA is concerned with the provision of online gaming FROM the IOM not into the IOM, there is nothing in this legislation that would affect hitting it big.