She now has my accounts set up with all types of rules and guidelines to simplify things.

Bottom line:Nothing is easy...the simplified federal tax code is 70,000 pages. 

Welcome to BiggerPockets, and thank you for such a clear, well-structured introduction.You’re navigating a situation many investors encounter later in their journey: strong equity, complex property condition, and multiple strategic paths.A few framing thoughts that may help:When a property needs heavy rehab, the central question is rarely “flip or hold.”It’s whether the numbers remain stable under conservative assumptions.Renovations almost always expand beyond initial estimates - not because contractors are unreliable, but because older properties tend to reveal hidden layers once work begins.Running scenarios with wider rehab buffers, longer timelines, and softer exit values can help you quickly see whether the opportunity is resilient or fragile.On the hold vs sell discussion:Adjacent properties can create real long-term advantages - operational efficiency, simplified management, and future optionality.

I’ve also found it helpful that the system connects directly to debit cards and automates expense categorization, so you don’t have to manually track every charge.As for Series LLCs — they can simplify ownership structure, but the best setup really depends on your state and insurance strategy, so it’s worth talking with a local real estate attorney or CPA before restructuring.

Access has some pretty easy tools to create forms, queries, reports and other objects, and a "switchboard manager" to greatly simplify setting up a main control panel.

I use a simplified version of this Template (https://www.notion.so/marketplace/templates/airbnb-welcome-g...) .

Though it sounds over simplified, keep this property in your portfolio only if you determine that you want to keep it.

Ideal for small down payments or rehab projects.Cash-out refi: Simplifies debt but not recommended right now while rates are 7%+.In either case, your equity gives you optionality when the time is right — a powerful advantage.📊 4.

Selling, taking the tax-free cash, and buying a home with an ADU/Airbnb suite in your new state usually offers a higher ROI and simplifies your life.

If selling simplifies things and reduces stress while setting you up better for the next property, that can be a rational move too.