I have been investing in the stock market for 5 years and I am now transitioning over to real estate after doing my research on real estate for the past two years. 

I had one short term rental that was granted a permit earlier this year and I have been operating it for months now as an STR.

- The Setup for Spring Season- My Skeptical TakeThe Weekly 3: News, Data and Education to Keep You Informed- Warnings flashing of ‘froth’ in crypto and stocks as S&P 500 valuation surpasses 2000 levels (BofA/Yahoo).- China is issuing record debt to stave off recession, while the US bull market continues (Wallerstein).- Texas vs California Home Construction.

If you know you want to invest in Real Estate, don't listen to those who advise you to invest in stocks.

Some design and amenity ideas:+ Welcoming living space with plush seating for family hangouts+ Coffee bar or stocked tea station for early mornings before campus events+ Dining table or breakfast nook perfect for family meals+ Dedicated workspace for parents who need to check in on workFor sports fans, tap into their game-day energy and make your STR the go-to spot for a fun, convenient stay:+ Big, comfortable seating & a great TV setup (think oversized couch, streaming sports channels)+ Game-day essentials like a mini fridge stocked with game-day snacks/drinks+ Outdoor space with a grill & seating for pre- or post-game gatherings+ Good parking (sports fans hate scrambling)+ Team spirit decor touches (subtle, not tacky—think framed sports prints, not full-on mascot murals)Your design & reviews will do most of the marketing but to market directly to these guests:🎯 List your STR on sites where parents and alumni book (if allowed)🎯 Partner with local businesses—coffee shops, sports bars, or tailgate services—where your ideal guests hang out🎯 Optimize your listing title and description with phrases like “Perfect for Visiting Parents & College Game Days”🎯 Time any discounts/promotions around major campus events—homecoming, graduation, big rivalry gamesThink of it this way, you’re not just offering a place to stay—you’re creating an experience they’ll want to book again and again.

Chicago is losing housing stock at an alarming rate. 

Stocks have their place in your asset portfolio but the available tax deductions are much more limited.  

Careful in the Stock Market, seems great on it's upward trajectory however...

They purchased a 25-unit building worth about $4 million through a short sale for $1.7 million.

I think this will be the short term realization, and anyone that did not wait on the sidelines and jumped in with the intention of a short-term re-fi might have to tap out.