Check their occupancy, nightly rate and amenities.

There are not a ton of comps on Zillow or other websites that I have checked and it was last sold a while ago so even these resources are unable to give me a quote.  

I've been checking HOA CC&Rs to make sure they allow short term rentals.

The right agent will have worked with Canadians before, will have lenders set up that can work with Canadians and will have a seamless process for management.Not only can an agent set you up with a GC, property manager, lawyer, insurance broker, inspector and everything else you need, they can analyze deals and put numbers in front of you.Your job as an investor is to vet the vendors they are providing and double check their analysis.  

I'll definitely look into the book by Pace Morby and check out his YouTube channel and Facebook group.

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

Check with an architect first to be sure you can fit your vision into the existing lot, as it's zoned currently.

Any other expenses are using up funds that would otherwise be sitting in your checking account to make a mortgage payment with.

If you're located in WI, check out Premier Point Realty and Homestead Realty....both offer the licensing course at a discount and some of the lowest fees/commission splits in our local market.

She has some stock (maybe 50k), some retirement IRA of around 100k which I believe she has started to take and then maybe 20k in her savings account.