Hey K.

Happy you found value in everyone's response here.

For your URL, I see your structure resemble a blog structure with your subfolder being "learn" instead of "blog". So if it is, your final URL that you described is fine (learn/buying-guide-for-inline-skates).
As a counterpoint, if you had this content as a hub page (some form of content pillar/topic cluster) for example, it would've been a good possibility to just change the URL structure since you have many Buying Guides. Different types of content, different ways to put it on your site. 
Like so: /buying-guide/inline-skates

At the end of the day, the structure needs to be logical and reflective of where your content is. I think you got it right anyway.

For the execution part;

1. I would not recommend using the "crawl as Googlebot" function in search console. It would be way too time-consuming for you, and it is not really designed for that kind of work.
2. Instead, update your sitemap with the final URLs and send it again via SearchConsole / Bing Webmastertools.
3. Also, don't forget to go ahead and change the internal links pointing to the old URL to point directly to the new ones or else you'll just have a bunch of 301's crawled by Google. Make it seamless.
4. Monitor. Monitor. Monitor.

Hope that helped!

And to add to that, Moz has a great resource on how to write them (emphasis mine);

• Keeping URLs as simple, relevant, compelling, and accurate as possible is key to getting both your users and search engines to understand them.

• URLs should be definitive but concise.

• When necessary for readability, use hyphens to separate words. URLs should not use underscores, spaces, or any other characters to separate words.

• Use lowercase letters. In some cases, uppercase letters can cause issues with duplicate pages.

• Avoid the use of URL parameters, if possible, as they can create issues with tracking and duplicate content. If parameters need to be used (UTM codes, e.g.), use them sparingly.

Source - https://moz.com/learn/seo/url

This is exciting! If I have suggestions for the tools, I will let you guys know.

Québec is indeed a great city, we are pretty proud of it! We usually organize the InboundMTL event in Montreal. We could hit you up along with some hubspot speakers and/or other agencies. Would you visit as a guest speaker or conference attendee?

Keep up the good work Rand, we are big fans!

Hey Rand!

Let me first congratulate you and your team for that awesome product that you guys succesfully delivered with time & budget constraint.

At the company I work for, we are using this tool for both english and french languages as most of our clients are situated in Québec, Canada. Since I do SEO in both languages all the time, how would you qualify your database for languages other than english (specifically French)? Are we looking at the same Accuracy? Are there problems related to suggestions & semantics?

Thanks a lot!

Hello Ruben!

Not too long ago, I saw a hangout with John Mueller who got the same question and gives a logical answer. Here's the URL at timestamp 46:06 https://www.youtube.com/watch?v=i_xnKznRNCc&feature=player_embedded#t=2766

I'd transcript if I had the time, but it will take you a couple of minutes. It essentially says that even though it is embedded, it won't access that block of content because maps.googleapis.com/robots.txt blocks it. If I understood wrong, please let me know!

I had the same problem where part of my content was coming from the pins INSIDE the map, but since it was blocked, it couldn't reach the content itself. Had to do a workaround

Hope it helps!

EDIT: Just jumping back in to say that you should look back at your site. Seems like Google can correctly crawl its own map and the content served through it. Our site has no more problems related to this. November the 15th I still had issues, but today I've tested multiple times and it looked okay.

Croy

Hello Ruben!

Not too long ago, I saw a hangout with John Mueller who got the same question and gives a logical answer. Here's the URL at timestamp 46:06 https://www.youtube.com/watch?v=i_xnKznRNCc&feature=player_embedded#t=2766

I'd transcript if I had the time, but it will take you a couple of minutes. It essentially says that even though it is embedded, it won't access that block of content because maps.googleapis.com/robots.txt blocks it. If I understood wrong, please let me know!

I had the same problem where part of my content was coming from the pins INSIDE the map, but since it was blocked, it couldn't reach the content itself. Had to do a workaround

Hope it helps!

EDIT: Just jumping back in to say that you should look back at your site. Seems like Google can correctly crawl its own map and the content served through it. Our site has no more problems related to this. November the 15th I still had issues, but today I've tested multiple times and it looked okay.

Croy

Hey Rand!

Let me first congratulate you and your team for that awesome product that you guys succesfully delivered with time & budget constraint.

At the company I work for, we are using this tool for both english and french languages as most of our clients are situated in Québec, Canada. Since I do SEO in both languages all the time, how would you qualify your database for languages other than english (specifically French)? Are we looking at the same Accuracy? Are there problems related to suggestions & semantics?

Thanks a lot!

This is exciting! If I have suggestions for the tools, I will let you guys know.

Québec is indeed a great city, we are pretty proud of it! We usually organize the InboundMTL event in Montreal. We could hit you up along with some hubspot speakers and/or other agencies. Would you visit as a guest speaker or conference attendee?

Keep up the good work Rand, we are big fans!

Hey K.

Happy you found value in everyone's response here.

For your URL, I see your structure resemble a blog structure with your subfolder being "learn" instead of "blog". So if it is, your final URL that you described is fine (learn/buying-guide-for-inline-skates).
As a counterpoint, if you had this content as a hub page (some form of content pillar/topic cluster) for example, it would've been a good possibility to just change the URL structure since you have many Buying Guides. Different types of content, different ways to put it on your site. 
Like so: /buying-guide/inline-skates

At the end of the day, the structure needs to be logical and reflective of where your content is. I think you got it right anyway.

For the execution part;

1. I would not recommend using the "crawl as Googlebot" function in search console. It would be way too time-consuming for you, and it is not really designed for that kind of work.
2. Instead, update your sitemap with the final URLs and send it again via SearchConsole / Bing Webmastertools.
3. Also, don't forget to go ahead and change the internal links pointing to the old URL to point directly to the new ones or else you'll just have a bunch of 301's crawled by Google. Make it seamless.
4. Monitor. Monitor. Monitor.

Hope that helped!