I would let him know any resources I know of that might help.

Deep cleaning + fresh paint touch-ups.People underestimate how much cleaner walls and crisp trim help the unit photograph better — and better photos = higher rent.5.

I like @Paul De Luca recommendation for option 2 because of the DTI situation and your overall goal of buying the next property.Either way, I don't think you can go wrong with either of those awesome Chicago neighborhoods, unless one is much closer or further away to the blue line - that could really help with your appreciation and long-term value!

Do you help them with that process?

@Stephanie DeppeHere's some helpful BlogPosts here on BP that will guide you on some of the different options. 

Ward III: How Mezzanine Funding Helped a Sponsor Close a $25M Multifamily DevelopmentWhen a multifamily sponsor in Texas faced a funding shortfall on a $25M project, traditional lenders capped leverage at 65% LTC — leaving a $4M gap between senior debt and equity.Instead of pausing the deal or raising more equity (and giving up ownership), the sponsor used mezzanine financing to fill the gap.✅ Structure:Senior Loan: 65% LTCMezzanine: 15% LTCSponsor Equity: 20%Term: 3 years, interest-only✅ Result:The project closed on schedule, equity investors kept a larger ownership stake, and the sponsor retained control.Takeaway:In today’s market, mezzanine can be the difference between “almost funded” and “fully closed.”

Because every winter there are storms and we lose power for a couple days and the pipes can freeze. 

It always helps to let the seller know your track record.

Looking forward to helping you and your client!

They're going to want to hear exactly what you need from them, and might be unlikely to help brainstorm.