Nothing will piss off the inspector faster than missing an inspection.My last piece of advice, in an effort to not make this a book length post, deals with the money.

Also, a few private lenders or hard money lenders might have some more creative terms for multifamily, especially if you're open to considering that route.

We were paying a bookkeeper $450/month, plus the $90 QB subscription to do our books but I felt like we were still having to tell her how to categorize everything so it just didn't feel like we were getting our money's worth.

We plan to make money on the properties.

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.

Driving relevant traffic to both a website and socials is hard without throwing some money behind it.

I mean really robust and to us the money is made finding those pearls of land that can be developed

I have cash reserves and money in retirement accounts, but I don’t want to dip too deeply into my reserves.

But you have the option to just pay the monthly payment up to maturity in case something goes wrong or if you decide you can use that money better to just build another property instead of paying it off. 

Do you want to be passive (ie give your $ to someone and they pay you interest, or you put the money for the opp and get equity, etc)3.