Happy to chat more over DMs if you’re interested.In general, the difference between co-hosting and full-time property management comes down to how involved you’d like to be as the owner.Co-hosting is a good fit if you want to stay engaged but offload certain tasks like guest messaging or calendar management.Property management is better if you’d prefer to be completely hands-off, with the manager handling everything including guest communications, maintenance, cleaning, turnovers, etc.However, there are two big benefits, in my opinion, to co-hosting over property management.

The kids assume they're getting a clean inheritance and start planning the sale to split the proceeds.

Some want a clean exit without discounting the price.

From there, adjust loosely for obvious differences like square footage, bedrooms, or major renovations, but don’t over-tune the numbers.For off-market deals where the seller is anchored high, having a clean set of recent solds is your best leverage.

Overall, the tax benefits of keeping it together are minimal, and selling or buying her out may give you better long-term results and a clean break. 

Regular inspections and scheduled maintenance (like cleaning gutters, checking smoke detectors, and servicing HVAC) protect your investment.Treating it like a hobby, not a businessTrack income, expenses, and receipts properly.

A clean offer with an escalation clause (e.g., "$2,000 over the highest verified offer up to a cap of $X") is pretty much standard.

Consistent execution plus clean reporting is what earns better money.

Nice work lining up the HELOC, that’s the hardest part for a lot of people.Even though you are no longer in WI, you can absolutely keep investing there; you just have to be intentional about (1) how cash moves from the HELOC into the WI LLC/deals, (2) how income is sourced/taxed in WI vs where you live now, and (3) keeping clean books as you scale.A real estate focused CPA can guide you through the best structure so you are not overcomplicating the entity/tax side while you grow.

On top of that, VA loans are great for buyers but they aren't always attractive to sellers due to stricter property condition and appraisal requirements than other types of loans and obviously they are not nearly as attractive to the seller as a clean, cash offer would be.