Well-maintained homes: Homeowners tend to spend more time and money maintaining their homes, which contributes to the overall quality of the neighborhood.

Not saying either is at their peak, but spend some time analyzing deals in both markets to see what you think for yourself.

Based on the questions you are asking I think you need to spend more time listening to podcasts like Bigger Pockets and Bigger Pockets Rookie.

I am wanting to be able to stop working full time sooner than later as I would like to be able to spend more time with my family and enjoy life. 

No need to spend an extra $1000 for something a tenant won't notice. 

I'm going to reiterate what's already been mentioned above, but I'm going to actually give you examples of why it's relevant to you to find a U.S. tax professional.1 - You're going to need to file U.S. taxes once you have property down here, there's federal filings, state filings, and sometimes local filings too2 - Tons of tax treaties between the U.S. and Canada that are easy to miss and can cost you a lot of money (important one with rentals - effectively connected income - if the professional you talk to doesn't know what this is, run away)3 - The amount of days you spend in the U.S. needs to be tracked and if you go over a threshold, all of your worldwide income could be taxable by the U.S.4 - Selling real property means up to 15% of your sales proceeds might not be available to you for years (FIRPTA)5 - Lots of nuance at the state and local levels, which both want to take as much money from you as possibleMain takeaway here is that you should find a U.S. based tax person.

Better to spend $60-80k for a conversion than over 120k.  

So, as a buyer I would not want to spend money before having a contract.

If I'm spending 500k... my profit should be higher? 

Example - borrower uses loan to purchase a home in a B or C grade neighborhood for 380k, spends 50k rehabbing primary home, uses 200k to put an ADU in the back, appraisal comes back at 925k.