The initial heartburn of lost reviews will likely be negated by more bookings (because guests don’t often like booking from large companies like Evolve) and hopefully better reviews with you as PM.

@Jonathan Greene Thank you for recommending Brian book.

(PS I'm sure you experienced folks have your contractors in line already but it never hurts to add another trusted one to the phone book, I'd love to send over our business cards and talk about how we could be of assistance to your team) Again thank you all for the help - Brennan 

I wouldn't worry too much about it, if you have a competent CPA or bookkeeper they should be able to review your books and within minutes have a strong grasp on who gets a 1099 (spoiler alert, not every contractor gets one, I'll be annoyed if I get one since I'm structured as an S corporation) and the amounts to report.1099 filings are usually a loss leader for us, so if you're working with a professional make sure you take advantage of them filing everything for you.

Educate yourself with books, podcasts, and courses, and consider partnering with experienced investors for mentorship.

Some landlords complained about having no bookings for months.

I have an Airbnb and an insurance adjuster who wants to book the place off Airbnb for two months.

Chad Carson has not one, but two BiggerPockets books sharing their expertise:Retire Early with Real Estate The Small & Mighty Real Estate Investor Exploring questions in his books like:How many rentals do I need to retire?

Right, I asked for books and a schedule for the biz from the return.  

Over the last three weeks I've read 7 of the real estate books and spent hours listening to biggerpockets podcasts trying to learn as much as a I can and narrow down my focus.