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.

Podcasts, books, and forums like BiggerPockets were invaluable, and when the right deal came along, I leaped and you can too!

Let’s say you’re starting from zero in 2025—no properties, no deals, just the knowledge and lessons you’ve picked from BiggerPockets, books you have read and videos you have watched.What would you do differently this time around?

(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 have been trying to educate myself through videos, books, and podcasts.

Listening to the Audio book of The Book on Managing Rental Properties.

The wonderful thing about furnished finder, which is what I assume you are using, is that you can book a property without being there to show the place.

(I remember when my dad bought some books from Amazon.com in 1996 or 1997; he wasn’t a pioneer, but he was a fairly early adopter, and immediately recognized the consumer value that Amazon brought.) 

You're better off reading the BiggerPockets forms getting a couple of books worth 100 bucks total and going from there.

I’ve been listening to audio books to get some ideas and every single one recommends getting on bigger pockets.