I think spending some time and resources on learning the House-hack or Flip strategies would be a game changer.

Here's a question for anyone who wants to play.

If you're going to need a mortgage, you're locked out of the game. 

That would be a game changer is you can use it to buy your second home. 

Hey BP,I’m relatively new to the industry with about 1.5 years of experience, but I’ve already learned that automating common tasks is a huge game-changer for efficiency.

Too many new syndicators think they can get away with skipping legal requirements—but the SEC isn’t playing around.If you’re raising capital, DO IT RIGHT:✅ Use a PPM & Subscription Agreement to protect yourself and your investors✅ Avoid general solicitation (unless using a verified 506(c) offering)✅ Understand accredited vs. non-accredited investor rules✅ File your Form D and comply with state laws🚨 Failing to follow these regulations could mean SEC fines, investor lawsuits, or worse.

This could be an opportunity to add value by offering to help with clearing or relocating those items as part of any potential agreement.Why This Could Be a Good Move for YouYou see long-term potential in the property, especially with the large lot and development possibilities (even if those are years down the line).As the current tenants, you have the advantage of a direct relationship with the landlord and familiarity with the property, reducing competition and risk.This could be a chance to lock in a property that you might otherwise lose if it hit the open market, especially in today’s competitive environment.Challenges to ConsiderIf the landlord is emotionally tied to the property or reliant on rental income, they may be reluctant to sell.Financing could be tricky, especially with today’s interest rates and the gap between the current rent and what a conventional loan might cost.The development potential you’re interested in is likely a long-term play, which means the property could be financially tight in the short term, especially if you’re only breaking even or slightly negative on cash flow.Structuring a Potential DealTo make this feasible, you’ll likely need to explore creative financing options that align with both your financial capacity and the landlord’s goals.Seller Financing: Propose a deal where the landlord acts as the lender, allowing you to make monthly payments directly to them.

If we sell, we will have between $150-200k to play with.

It's unclear on how that plays into your question about taxes.

House hacking in Chicago can be a game-changer—letting you live for free (or close to it) while building wealth through real estate.