I had the initial call with a PadSplit sales person, but I wanted to talk to somebody who's actually doing it to get their perspective and advice.

I continue making the underlying mortgage payment myself (autopay) and get reimbursed from the borrowers payment.

Talk with your tax pro or reach out to my company for help

What will happen is you'll continue to waste time being drawn into the tenant's circle of drama.Just stop engaging.

Make sure you talk with your insurance company on what you would need to faciliate these types of amenities in your rental.

Then rent the bigger home out using a property manager, allowing her to possibly cash flow and maintain that asset and let it continue to grow in value.Encourage her to consult with a CPA or tax attorney to explore the best strategy tailored to her situation.

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

Whether you sell and simplify or hold and continue to benefit from appreciation, it’s about aligning with your long-term goals and lifestyle.

Try to talk to a lender or two to get a real concrete idea of what you can do.

No verbal talkie-talk on it, no, send it over WITH the amendment for them to sign.