when is it a good idea to get a lawyer?
Only when you are not confident that you can put enough dedication to the matter & learning curve, or when you are not confident of your ability to cope with the emotional/frustrating toll of judicial proceedings. I do not mean this in an ironic way or to challenge you. It is just important to avoid a false sense of confidence.
However, if you decide to represent yourself in court, you will have much more control of your case than if you delegate it to some lawyer whose attention is split with many other unrelated cases.
Also, never get intimidated by pedantic or wasted phrases such as "he who is his own lawyer has a fool for a client". In the XXI century, most urban people can read and write, Canadian laws are written in your own language, and the Internet provides many informative resources for free. Furthermore, even knowledgeable attorneys happen to be clearly wrong about the law, as I pointed out here.
I feel like the bulk of the work is carefully detailing what happened
which feels more like the job of a news paper editor.
It involves more than that. A newspaper editor does not get entangled with subtleties of a story or of the law, and subtleties are often decisive in judicial proceedings.
Litigation also involves intensive legal research so as to find case law (that is, binding court decisions) and statutes that support your position. The application of these laws to a particular case are often premised on subtleties. Hence my remark in the previous paragraph. A newspaper editor hardly ever knows what questions or evidence are required or would suffice for proving a case. This knowledge only comes through (self-)education and experience.
What options exist if I don't want to pay a lawyer a bunch of money
and am willing to do most of the work myself, for example would pro
bono be a good option?
Start by searching for "pro se" and "Canada" on the Internet. Some of the results might actually provide guidance on what procedural law(s) apply in your jurisdiction, the legislation, and so forth. As for searching case law, there should be a Canadian equivalent of http://www.leagle.com/leaglesearch (sorry I am not knowledgeable of the specifics of Canadian litigation/resources).
Based on your other post, I presume you are or will be getting acquainted with the Tenancy Act. I recently addressed here a question about the Act, showcasing the combination of that legislation and contract law (interestingly, many tenants presume their issue with the landlord is strictly about landlord-tenant legislation when in fact it has to do with contract law).
I am sure in a library will find plenty of useful books covering the basics of the legal system as well as the rules of civil procedure.
Find out whether the public has access to case files in Canadian courts. If so, go to a courthouse and study those files. Get acquainted with the drafting and format of pleadings, motions, responses, briefs, and so forth (although in Small Claims court much of this would be unnecessary, for small claims proceedings are much more simple). This will show you the practice aspect of what you learn from books.
When using a term that you consider essential to your case, be sure to consult its meaning in a legal dictionary (I do not know whether Black's Law Dictionary is applicable in Canadian litigation). The meaning of many words are much more specific in litigation compared to their common usage.
Or would getting a real lawyer and spending only one hour of his time
I highly doubt it, especially if you have not gained any background in law. A lawyer will not explain things from scratch, let alone the intricacies you need to know.
The most you could get from speaking with a lawyer for an hour would be notions which are too generic to be of any use at all. Moreover, I doubt that a lawyer in a phone interview will give you any legal references for you to verify on your own.
In the very beginning of my litigation, I spoke with a law firm as assigned by a lawyer referral company. By then I already had some background in law and therefore I had specific questions. The guy from that law firm just kept babbling ambiguities very quickly. At the end of the phone call, I thought "nah, I will do this by myself". You might end up making that decision in your current or future matters.