If anyone else has a favorite strategy or tool they use to keep tax prep under control, I’d love to hear it!

How good of a deal would be needed to make this strategy work? 

If you’re not satisfied with your current attorney’s approach, it may be worth seeking a second opinion to explore other strategies or angles you might not have considered.Next, focus on compliance with housing codes and tenant protection agencies like DCF.

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

Has anyone used the company BNB Leverage to help with the airbnb arbitrage strategy?

The seller will always retain the equity and would receive annual distributions - and could structure the agreement with an exit strategy that makes them comfortable. 

Additionally, these properties generally attract long-term tenants with longer leases, offering more consistent cash flow

They have a brand they're trying to keep consistent over the entire portfolio.

@David MartinezA quick search on furnishedfinder.com shows a bunch of available midterm rentals in that area so you can use those to help guide your price and strategy.

As others hinted 20K does not leave you a lot of room and would narrow down what strategy you can use.