How can I go about repairing the indexing on some of our webpages?

Typically just moving from one server to the next has no issues at all so long as you're not making any other changes to the site, such as changing URLs in a re-design process. Just make sure its a quality, respected server. If the server has issues then, yeah, you'll inherit them. But otherwise you'll be fine.

Two key concerns are 1. Customer confusion with the 2 offerings: Imagine being in an art gallery that sells photography training and fine art or a book store that tries to sell you fine art. Even if it's the same group of people, they may be in very different mind-sets and hence may not associate both together. 2. SEO challenges with mixed messages you're sending. Which keywords would you optimize for which part of the site? Advantage would be if the customer base is the same group of people, hence offering cross-sell opportunities. For instance, if your MAIN source of leads for the training site is the art site, then this would be more important. In general, I would suggest one site for one customer group. If there is likely to be a very high overlap, then same site, with multiple sub-sites might work. In matter of fact, it'll probably be EASIER to do two sites for this than one site. Your designer will thank you :) Then tastefully add cross-links in the places where someone is likely to use them. For instance the art gallery could have a post 'How I make art' and links to your other business there. And the photog training site would have your art pics with subtle on-image links to your art biz. While I'm not a branding expert, I do find that my engineering lead approach to challenges in Marketing/Sales usually works, and provides clarity and direction.

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

The cost of SEO depends a great deal on three things: 1) The specific services being offered (SEO, social media, content strategy, etc.) 2) The degree in which those services will be implemented (how many hours per month) 3) the skill and experience level of the SEOs involved. $800/month is a pretty small investment if you consider all the layers to making a web marketing campaign successful. My company will usually not touch any fully-managed web marketing campaign for less than $1500/month and that's at the low end of the aggressiveness meter even for a pretty basic site. A larger ecommerce site might start around $5K and go up from there. Overall, you want to look for value and results. You'll want to know how long the SEO has been in business and when looking at proposals you need to understand the amount of time the company will be investing in the campaign. You also want to spell out your goals and establish the expectations on how/when those goals will be achieved. When the SEO and client don't have the same expectations, that can lead to issues later on. But if you know what the goals are you can both be on the same page from the start.

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.