I also plan on creating a phone app this year that further simplifies the sytem.

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.

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

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.

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

Would be nice to simplify.

-based)Handles motivated seller calls and negotiations.Covers all five virtual markets.Works directly with JV partners when needed.1 Operations ManagerOversees systems, troubleshooting, and process flow.Coordinates with acquisitions manager and VA to ensure deals close smoothly.Strategic Realtor PartnershipsRealtors in each market handle MLS listings.Dispositions simplified: instead of a full-time Dispo manager, we leverage agents + our contracts.VA supports transactions by communicating with title companies, buyers, and sellers.Volume & ResultsWith this streamlined model, my company consistently closes 5–7 deals per month across multiple markets.

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

On the rental side, since that interest is deductible, the real cost is lower, which makes it less urgent for some people to pay off.I’ve also seen investors in similar positions separate “sleep-well money” from “opportunity money,” where some cash goes to simplifying the balance sheet and some stays liquid for deals that require speed.