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.

you need a big funnel for any strategy in which you evaluate leads, and to continuously be ruling deals out - and to be happy you're doing so, not frustrated. 

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

I would be happy to setup sometime and talk strategy if you would like. 

I think in any market the best way to buy right is to find an area you like and canvas that area with letters, calls and door knocks, getting out and talking to people.

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

Is there any ever any confusion for the guest as to who they are talking to? 

It would be good to talk to a lender to make a game plan and review your financials.