Looking At Chicago Investing Differently with Jason Wagner

Looking At Chicago Investing Differently with Jason Wagner Jason Wagner Shares New Ways to Get Deals Done In The Chicago Market Buy and Hold Rentals, House Hacking, Partnerships, Assumable Loans, 2/1 Buydowns Jason Wagner, Managing Broker of Greystone Realty, is a seasoned agent and investor who has built up a sizable portfolio using various creative strategies. Jason shares why he chose to invest in Chicago’s northwest side and how he’s achieved success in that area. He breaks down assumable loans and 2-1 buydowns including how these tools can be leveraged to improve an asset’s ROI! Jason discusses the power of the data he compiles in the Wagner Report and how investors can utilize it for a competitive edge. He closes with bullish remarks on Arlington Heights and powerful advice for new, aspiring investors! 00:00 – Kicking off with Jason Wagner and what’s new in his business 03:00 – The importance of handling utilities during tenant turnover 05:00 – The Chicago Bears’ Arlington Heights move and its market impact 08:00 – Why Arlington Heights may be one of the hottest suburbs in the U.S. 10:00 – Chicago’s Northwest Side investment performance: Portage Park, Belmont Cragin, Jefferson Park 11:00 – Explaining 2-1 and 3-2-1 buy-downs and how to use them 13:00 – How Jason partners with clients to co-invest in properties 16:00 – Low inventory and the importance of acting now 18:00 – Why Chicago prices keep rising while national headlines say otherwise 20:00 – How tax benefits and cost segregation amplify real estate returns 24:00 – Why cash flow isn’t everything — equity and depreciation matter 27:00 – The 100% ROI example of owner-occupant leverage 28:00 – Understanding FHA and VA loan assumptions 30:00 – How assumable loans create new opportunities for buyers 33:00 – Selling properties with assumptions — and skipping appraisals 35:00 – Why “2% debt is the asset” and how blended-rate loans work 36:00 – The story behind Greystone Realty and its investor-agent model 38:00 – How owning rental property changed Jason’s approach to clients 40:00 – Identifying riskier neighborhoods by months of supply 42:00 – The Wagner Report: using data to predict Chicago’s next moves 44:00 – The Midwest advantage — why our fundamentals are stronger 46:00 – Arlington Heights’ downtown, entertainment plans, and livability 48:00 – Jason’s passion for 75 Hard and personal growth 50:00 – Advice to 20-year-old investors: buy the first house hack now 51:00 – Book recommendation: The Five Levels of Wealth by Sahil Bloom 54:00 – Jason and Rachel’s Real Life Investing Podcast 55:00 – Final thoughts and resources for Chicago investors If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Join us as we share our winning strategies, success stories, obstacles we've encountered, and most importantly, the lessons we have learned along the way. If you are ready to learn the ins and outs of the investing in Chicago and suburbs. SUBSCRIBE: http://ow.ly/pNzU50BFJtU Got an idea for the show? Shoot us an email at straightupchicagoinvestor@gmail.com Follow us behind the scenes on Instagram: http://ow.ly/lquy50BGadL Make our acquaintance on our Club: http://ow.ly/RZvr50BGaei Give us a shout on Facebook: http://ow.ly/Qqr350BGaeM Visit our world directly: https://www.straightupchicagoinvestor.com/ Listen to the 𝗦𝘁𝗿𝗮𝗶𝗴𝗵𝘁 𝗨𝗽 𝗖𝗵𝗶𝗰𝗮𝗴𝗼 𝗜𝗻𝘃𝗲𝘀𝘁𝗼𝗿 𝗣𝗼𝗱𝗰𝗮𝘀𝘁 on your favorite streaming service: http://ow.ly/lI7050BGafp