Hi Everyone, I own and manage a 5-star STR in northern Wisconsin in a resort area. I've been following Ryan and his team since the beginning of my journey. We aren't the typical Ryan Bakke follower... My husband and I left our high-paying jobs to move to the Northwoods to buy and run a resort, but when we couldn't find any that fit our wheelhouse, we switched to lake properties. That was also a struggle as many aren't built to our standards. But we did find one we liked, and after closing, spent 18 months renovating it. We did most of the work ourselves (I'm a creative and my husband is in construction). I currently manage the bookings, cleanings, marketing, guest communication... my husband helps with turnovers and maintenance. We are about 85% direct and booked nearly 100% from the beginning of June through the end of August. Fall is usually 50% occupancy, but the other times (spring & winter) are very low. We have not found another property that cash flows. Since then we've started a caretaking business, a mobile sauna business, and some remodeling/design work to make ends meet. In January my husband took a full-time job to supplement our income. We're about to purchase a local business, likely by the end of the year, that we'll both work at. This is will our main source of income. We have not had good luck with tax preparers/CPAs, even though I thought I was asking all the right questions in the beginning. This year, because of what I learned from Ryan and his team, we amended our 21 and 22 taxes, and 23 & 24 are being finalized as we speak. We hired a capable bookkeeper and I got our current CPA to file Schedule E and reclassify some of our capital investments into shorter lives. I've spent countless hours learning about all of this to the best of my abilities (I'm a creative, so no small task!) and feel good about our progress. But now we're moving into a potentially much higher income bracket and we're ready to really lean in even more! - Why do you want to save money on taxes? Not just “to save money” — but what does that money mean for your life? ••• We want entrepreneurship to look doable to our child (vs. really hard, which is how it appears right now). We want to live in a nice house again. We want to travel regularly. - Where are you right now in your journey? Just starting out? Own rentals? Flipping or doing STRs? ••• See above. - What’s your #1 challenge right now — your “big domino”? The one thing that would make everything else easier? ••• Finding an operator. We're in a resort area, so oversaturated with vacation rentals and lacking capable, trustworthy help. I would like to hand over the reins, but keep the total 5-star experience, something that currently sets us apart from our competition.

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?

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.