What is the best way to configure a site/pages so that it has the best chance of ranking in multiple (2) countries on Google?

If you got 5000 sites to link to your site using the same keyword you'll likely be flagged for spam and attempting to manipulate the search results. That is an old-school attempt at SEOing a site that Google and the other search engines have already developed algorithmic answers to. There are three aspects to building up your search rankings. 1) On-Site Optimization: Your site has to be coded in a way that is search and mobile friendly. You need to optimize your content for searcher's topical interest's (keywords), and give your visitors a great on-site experience by focusing on usability issues. 2) Content: You need to create and publish awesome content that fills the needs of the audience you're trying to reach. Write blog posts and create other forms of content that answer questions, provide tips, and map out solutions that truly illustrate that you are an authority on the topic. 3) Social Engagement / Links: Links are an important part of the algorithm, but getting a bunch of sites to link to you using keywords is the wrong approach. You need to be engaging on social media and (to a far lesser extent) socializing your content above. But the more you engage, the more others will socialize your content for you, which is where authority is really built.

I have been working in SEO for over 10 years and have built search agencies from the ground up. I've also worked with some big brands on International SEO like Active.com, as well as many US based chains like Extended Stay Hotels. I suggest sub-directories as they are MUCH easier to manage and promote via SEO. You can't have specific local IPs with sub-directories, but you can with sub-domains. But that's not hyper critical, there are WAY more important factors. Plus, you can geo-target in Google Webmaster Tools. Your current structure for sub-directories is perfect: http://drivingtests101.com/Canada/Ontario With subdomains, each will be treated like a brand new site. So you would have to work very hard to get each to gain good authority SEO-wise. Plus managing and hosting lots of subdomains is a ton of work! In order to not get penalized you need to: Implement the the "lang" and "hreflang" tags in the HTML of each country directory and all pages within. Have unique Title tags and descriptions written in each language. Have unique content for each country and state page. Written in each respective language. Yes, its a TON of work but hey, you are trying to take over the world! If you are serious about international search traffic then you will do these things and the costs should be balanced out with the extra traffic you'll get. If you can make the root domain super authoritative then it will boost ALL of the internal pages. This is also key to ranking well for international search. I'm open to a follow up call to elaborate on any of my responses or to answer other questions.

Obviously, no 2 situations are alike; and multiple factors affect any outcome. Practically, the number of answers is infinite. But one factor I've looked at intensively, full time for years is the role played by the brand name and/or the site's domain(s). Think of doing business -- online or off -- as moving along a path. Some paths are rocky or go through quicksand. Others can be made straight and smooth. Obstacles can be cleared, or the surface may be lubricated. For most niches, you'll see brand names / domains that add friction -- friction that is compensated for by extra marketing inputs ... effort or money. Suppose your niche were nicotine patches. Well, ideally you might own NicotinePatch(es).com to simplify brand recognition, add trust, increase click-through rates, and so forth. Traffic can be built up without an exact-match domain. No doubt about that. Still, not all domains / names perform equally well online or in the minds' of an audience. Answers aren't always so clear cut. However, since the internet is built on domain names, domains and names are worth evaluating very deliberately.

The best way to work around something like this is to map out the long-term strategy in phases. Build out a brief project map that outlines what they will receive within the 1-3 month period, the 4-7 month and the 8-12 month period. Set micro objectives for each period and this will give the client a bit more confidence in the short-term plans as well as the long. The key thing to remember here is that the client will often be worried about being tied into a contract that doesn't deliver results. As a result, you need to show why you need the time that you do. One thing that I often throw in is an extra incentive for longer contract lengths - for example, an extra PR/content campaign or some paid advertising extras. Try to assure them of some shorter term results that you can obtain as 'quick wins' and build their confidence this way - the major targets will always be longer term but if you can demonstrate that there will be progress between then they will be a lot more receptive.

TL;DR -> Yes you will risk it if you don't perform a proper audit and migration from the original platform. Any type of architecture changes can 100% ruin your SEO if you are not migrating content and topics correctly. Many people assume this is limited to URI structure but underestimate the power of Topical hierarchy and the content, internal linking and URI structure which play a crucial role into any migration effort. If you have any questions about the migration process, give me a shout. Decent free migration checklist: https://searchengineland.com/site-migration-seo-checklist-dont-lose-traffic-286880