Our HOA is considering buying the lease so that the entire condo will become fee simple.

It's a business decision for you to make, everything has pros and cons.Yes, just list on STR sites with 30 day minimum, simple and done.

So is this just as simple as showing how much the property makes or do they also look at personal debt to income, credit score, reserves etc as well.

Speaking from hands on experience on both platforms as I've worked with both Carrot and Wordpress sites (more than 400 sites so far since 2017), what carrot brings into the table is their simple, all in one, fast website platform.

And remember the REI Simple Program that you signed up for but didn’t use?

Trying to keep things simple with long-term single family rentals til I hit my conventional limit then will try different strategies with different funding options.

If you have ever learned something important by trial and error, then you can probably understand the frustration that you feel when you make a "rookie mistake" or a simple error that creates a big negative result.

, and I’ll need to have the series name on the property deed (is that as simple as naming it “123 Main St, and having the deed as “123 Main St, a series of My LLC”?).

Relatively simple installation as no walls were damaged. 

Alternatively, in a QBO Simple Start or Essentials subscription, if seeing profitability by property is important, you could still structure your chart of accounts to reflect each home, though your P&L will be a bit more lengthy & harder to digest.If you have any questions, feel free to reach out, happy to walk you through the pros & cons of QuickBooks options!