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.

We feel this encourages/trains good payment behavior:)We have several MoveIn Specials owners can approve like, free TV, Washer or Dryer (used), etc.Our main goal with MoveIn Specials is to stand out from our competition. - Just lowering the rent really doesn't do that.

Because there is tons of competition for flat fee brokers for as little as $99.

As others have noted credit unions are generally competitive on HELOC's. 

As a full-time student living on campus, I’m looking for part-time opportunities that could help me gain some experience in the real estate industry while also make a little bit of money. 

Seller financing can be a fantastic way to get into a 4+ unit property, especially in a competitive market like Chicago.Have you started reaching out to owners directly or networking with agents who specialize in multifamily properties?

That means that there is now competition between hosts and you have to give people a reason to book your unit over another hosts.

Check Furnished Finder, Zillow, as well as AirBnb and VRBO (30+ day stays) to see what sort of competition is in that specific market.

A knowledgeable attorney can advise here.Create a solid operating agreement: Since you own the condo with a friend, a clear operating agreement is essential to outline responsibilities, decision-making, and profit-sharing for the LLC.To save on costs:Look for real estate attorneys who specialize in investment properties and might offer package deals for the retitling, operating agreement, and filing the LLC.Shop around for title companies that can handle the transfer smoothly and provide competitive rates.Research DIY options for setting up the LLC if your situation is straightforward, though I’d still recommend a lawyer for the transfer process itself.Good luck with the process!

I don't disagree that Airbnb claims can be difficult but this is all very common in the industry.