I never bank on appreciation, but I try to invest in neighbourhoods where appreciation is headed

I’m looking for someone who has real experience owning or investing in commercial properties, ideally with knowledge in: • Creative financing (seller finance, private money, hard money, SBA) • Evaluating distressed or value-add buildings • Mixed-use / retail / restaurant build-outs • Deal structuring & due diligence • Understanding liens, zoning, and permitting issues.I already own commercial property and manage tenants so I do know some things, but I just need a knowledgeable, quick consultant/mentor who can help me validate my numbers, risk, and strategy on a time-sensitive deal.

But in this city, your financing strategy can make or break your deal.Here’s what investors should know about buying, selling, and financing property in Chicago right now.Why Chicago Remains a Strong Market for Real Estate InvestorsChicago offers a combination you rarely find in other major metros:• Affordable entry points• Strong rental demand• Older properties with consistent value-add potential• Diverse neighborhoods suited for nearly every investment strategy• Appraisal upside in revitalizing areasNeighborhoods like Avondale, Bronzeville, North Center, Uptown, Albany Park, Portage Park, and Rogers Park continue to offer a mix of appreciation + cash flow opportunities.Financing Determines Your Strategy — Here Are the Top Programs Investors Use:1.

This is the whole key to buy and hold investing (the brrrr method in particular)What some investors like to do is what we call a diversification exchange, where you sell one investment property and invest in multiple smaller investment properties in a 1031 exchange.

Bank financing is available from a local credit union or bank, but dont be suprised if the bank cuts you off at 60% LTV of the ARV

For your team:Attorney: I’d prioritize someone who does RE closings in Kingston/Catskill every week and is comfortable with inspection/contingency issues on older properties.CPA: Local is a plus but not mandatory, what matters most is that they’re real-estate focused and understand NY rules, depreciation, entity options, and how this first property fits into a longer-term portfolio.Bank: Call a couple of local/community banks and ask specifically about how many investment property loans they do and whether they keep loans in-house.When you’re interviewing anyone, I’d ask, “How many small investors like me do you work with, and what do you wish they asked you before buying their first deal?”

A HELOC or HEL is usually the best move because you get to keep your low 3.87 percent first mortgage, and the interest is typically deductible as long as you use the funds for another investment or rental project.

This is all assuming the seller is selling an investment property and you are buy it as one. 

I have been looking into investing remotely there and wanted to get a heads up on the good and bad etc.

@Chris McNamaraa lot of green flags in your post compared to others so that's great.but just to challenge you a little... why not invest in MA or within a couple hours of where you live?