Hoping to get some answers regarding LLCs: 1. We have one LLC that owns AND OPERATES our STR. First, I'm wondering if that's okay. All purchases go through that business, all rental income, etc. We're starting year 4 with this set-up. IF this is not ideal, how do we fix it? 2. We're about to purchase a business and the real estate the business occupies (2 separate purchases). The service business will rent the real estate. Each will have its own LLC. Can the RE part of this sit under a holding LLC along with the STR LLC?

Dear community I would like to get your thoughts regarding setting a single member LLC as the STR owner. I understand it helps with liability issues but it also increases complexity in terms bookkeeping, separate finances, state reporting, etc. Is there any other LLC benefit I’m not considering? Thanks

Our property went in service in August 2022. We did most of the renovations ourselves and kept very good records, so put appropriate improvements into shorter life accounts in QBO (FF&E of course, but also floating floors, carpets, removable wallpaper, all 5-yr; plus septic, well, landscaping as 15-yr.) Does it still make sense to do a CSS now—in 2025? The pro-rated improvements of the original purchase price is only $253,218 (land is $ 201,781) although the property is valued at probably $1.5M now. We are planning further improvements on the building, such as windows, roof and added insulation.

What accounting software does everyone use? From time to time I see a new product pop up in this space and its tempting to be distracted learning new ideas. Clearly we can't pivot for every cool new software idea, so Im curious if folks could share their fav and why?

Hey guys! I’m Matthew. I’m a proud dad of two awesome teenage boys. I currently reside in Illinois. I’m a real estate investor and I also run a 7 figure contracting business. I'm here to soak up as much as I can about taxes and hopefully make some new friends along the way. Drop a comment and let me know what you do and what market you’re in so we can all get to know each other better and maybe even team up on something down the road. Glad to be here!