I run a real estate company and we pay a lot of contractors for all types of things, work related to flips, inspections, running errands for us, surveys, etc. It's my understanding that any person/LLC we pay (Cash, Zelle/Quickpay, Check) over $600 that IS NOT an S/C Corp, should get a 1099. We've never done this. We still write those costs off as expenses (because they are), but we've never collected W9s from people we work with, or created a 1099. What's the risk here? It's my understanding that the risk here is that we can get penalized for this, but from a tax perspective, we can still write off those expenses and it doesn't affect anything there, is that right? From my understanding we'd have to issue 1099s to the following folks: General contractor Sub contractors Survey company Inspector Cleaner Anyone that gets over $600. Before we pay them, we should be asking for them to fill out a W9, right? Am I missing anything? I watched the video about this.

Hi all, My wife Dominique and I are new to the group and new to STRs in general. I'd heard there are several other Smoky Mtns investors here, so I'm curious if anyone has a cleaning service and/or handyman that they would recommend? We live in California, so we're hoping to find some very trustworthy "boots on the ground" people or services that could help us keep our investment in great shape between our in-person visits and respond to guests' needs. We welcome any and all suggestions, and thank you in advance!

We are w-2 based income and have a secondary home we rent to cover basic expenses. I’d like to learn how to convert the property to a compliant STR and get a Cost Seg Study completed to take advantage of bonus depreciation and active losses to reduce our active W-2 income.

New community member going through the classroom videos and lessons while also working to get all my documents and forms completed so I can schedule my first call.

I am new here but I have gone through all Level 1 and Level 2 and then realized although I received all the info and trng the meter did not move from 0 once I got to level 3 and the system said I had not finished 1 and 2. Any idea on what I am doing wrong?