If the Arua Municipality by-election and its violence were to teach us anything, it is that Bobi Wine's major challenges moving forward will include trying to stay alive, and also keeping out of prison.
He could be taken out in a street shooting - sheikhs-Kagezi-Kaweesi-Abiriga-Kirumira-Entebbe women style - or poisoned and killed softly. It is also easy to cook up charges and lock him up without bail for the next two years - and be released on election day or a couple of days after.
However, if he were killed today, it is uncertain there is enough momentum for his death to excite protests across Kampala - and Kampala is enough - that could overwhelm Mr Museveni. [Besides, Ugandans are generally cowardly, and too poverty-stricken for sustained street demonstrations].
On the other hand, if he were jailed, it is difficult for his jailing to bear fruits as promptly as it would when he were on the streets running, singing and talking. Thus, staying alive, and being free to circulate about, and release more music are the best things he has to protect jealously and carefully.
Against that, it is unlikely that by saying he was considering challenging President Museveni in the forthcoming election, Bobi Wine believes he can win the election and take the presidency.
That is not the way revolutionaries leave office. With a state that is deeply militarised and privatised - with willing sellers and willing buyers - it is difficult to imagine Museveni's powerful generals - including his son, in-laws, and distant relatives - who have so generously benefited from his presidency standing and saluting a skinny lad and former entertainer as their new president.
How about the merchants (or are they thieves?) in Nyekundire circle, and other poachers eying oil and gold? Not even Museveni believes Bobi Wine on electoral candidacy. Declaring candidacy was nothing outside personal safety and continuity outside of the coolers. What else could Bobi Wine say or do to remain active?
Despite constantly reminding compatriots to pick their national IDs (a thing that has ironically unsettled government to the point that if it were not for big capital, it would have been stopped) he has refused - for all the right reasons - to form a political party.
Not that there is a direct connection between IDs and political parties, but to have a serious challenge in a nationwide election, one has to have structures through which an election is coordinated and protected from theft. Secondly - still for the right reasons - Bobi Wine, with the exception of a few handlers composed of his usual music crew, close buddies and family, does not have a team of experts and strategists thinking through his next steps.
With the exception of a committed photographer, the fellow personally handles his social media activities. The upside of this is that it has allowed him the freedom to continue his free thinking - as an artistic intellectual.
Surely, this does not look like a man "seriously considering challenging" Museveni in an election. His apparent "lack of seriousness" about the ingredients that go into winning an election - despite the loud declaration - should be seen as Bobi Wine's strategy.
With a regime that is extremely dangerous to opponents, one has to remain as legal as possible. The Museveni government has showed us how good it is in finding exploitable illegalities against opponents and have them consumed in endless court battles and, oftentimes, imprisonment.
To this end, even when he may not believe in the election nonsense, Bobi Wine could not say anything otherwise - say, mobilise for street protests in the Kizza-Besigye tradition (see also, Khartoum, Cairo, Algiers, Kinshasa or Harare).
This awareness, that he has to fight to live, coincided with his otherwise rising star - in part, propelled by two violent by-elections in Bugiri and Arua, and general mass fatigue over his mentor, Col Besigye. With politics being a game of the moment where one has to seize their time and scale it forward, Bobi Wine has had to declare a bid for the presidency.
Readers have to look outside the election box as a mere means of challenging the incumbent. If you were Bobi Wine, the election means raising the stakes of your life, and potential imprisonment.
Killing or imprisoning you must be costly enough. And at the end of the day, there's only one thing that Bobi Wine can deliver to his adoring fans: overwhelming the dear leader into standing down.
The author is a PhD fellow at Makerere Institute of Social Research.