Hi Joel,I am interested in start doing the same as you to be using it for medium term rental (28+ day stays) arbitrage in GTA (as short-term rental stays (less than 28 days) are restricted).

If I were starting out now, I’d focus on markets that balance affordability with solid rental demand, both for short-term and long-term rentals.

I am about 1.5 hours from Pocono’s with 2 short term rentals there.

I probably wouldn’t mention your third point - it makes it sound like you expect them to hold this note forever and I’m not very certain, but I’m guessing there isn’t a huge market for $100k secondary notes.Have you considered asking them to finance 90-100% for a short period of time so you can rehab and refi at a higher valuation?

You can do a trial and see if bank feeds connect, if it does, I would then recommend using it over QBO.One of my client that just started in development is short on funds so Xero was the only best option and they are using a local bank so we couldn't connect and a lot of manual entries. 

but generally - new accounting and property tracking softwares fall short in one of two places: 1) they don't actually generate financial statements that a CPA or Lender will approve, or 2) They can, but the learning curve is so steep or convoluted it's impossible for you to get help if/when you need it (I imagine this is why this thread is a little slow right now)Have you asked your accountant what they think will work best?

Like someone else mentioned, doing a short term rental in a secluded basement that is very private and walled off is one thing, but sharing the same refrigerator, kitchen thermostat, etc. with a complete stranger seems like it will introduce more problems than what the money is actually worth.

STRs in Massanutten - looking to connect w/someone on discussing what a reasonable offer on a STR out here would look like. Also, if you're a serious end buyer and can cover the first part, that would save a step. Not...

I have actually been considering Grenada's and Barbados' viability for potential short-term rentals.

The numbers I’ve been running look really promising from a short-term rental (STR) perspective, and the area seems to have favorable STR regulations—or at least a lack thereof.