Thanks guys!

Yes so it looks like Venmo will only send a 1099-k if the amount paid is over $20k but the IRS has a different requirement. Which then in my mind means I still have to issue a1099-NEC. So if this cleaner won’t give me a W9, since I have not paid her more than $600, I need to find a new cleaner. As Mason points out, why would I want to do business with someone trying to fly under the tax radar.

I use QBO for my husbands business as well as the QBO payroll, my little bookkeeping business, and our long term ental LLC. Plus my clients are on QBO too. I am interested though in software for the STR business when we actually pull the trigger.

Hi there! We live in Mars, PA (north suburb of Pittsburgh). My husband is a licensed psychologist and has his own med-large private practice. We are partners in an LLC that owns one LTR property. I am a finance director for his practice, but also have my own LLC in which I provide bookkeeping services to just a few very small clients. 1) Why save- we are 54 and 52 years old, kiddos are off the college payroll so looking towards the retirement ages. However, we pay a lot in taxes. We are looking for ways to offset our W2 income to reduce taxes so we can use those funds to further diversify our portfolio. 2) Where are we - we have the LTR which is easy peasy because we rent it to the psych practice. However, I have always been interested and intrigued by real estate so I am turning my sights on an STR. 3) Challenges - we just engaged Ryan's practice as our tax strategist and I just joined Bill Faeth's Inner Circle. I am overwhelmed with info from it all. Plus here we are in mid-October of the 2025 tax year and I feel frazzled in this 4th quarter push. And, we are going to PCB in two weeks to look at STR potentials and that process of just picking things to look at is overwhelming.