I have a few options in play right now for my goal of adding another property to my portfolio this year, it seems like the Chicago market is yelling at us to invest into single family homes in B+ areas.

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.

Having it solid in a spreadsheet instead of in your head or on notebook paper and playing with the numbers for the repair budget isn't wrong.

It’s always interesting to see how people’s backgrounds play into their investing strategies.What kind of multifamily properties are you eyeing right now?

There are many good locations - I'd suggest that you play around with the "Market Finder" tool at the top of the screen here, included with your pro membership. 

Yes, having tenants pay ACH via a Tenant Portal software is best, but not all will cooperate and some will play games that result in NSF charges.We allow tenants to deposit cash/check/money order directly at our bank into our account.Many Class C & D tenants have challenges adapting to unfamiliar ways to pay and is often not worth the hassle (and possible evictions) to get them to change:(

Lease options are another play, where you rent a place with the right to buy later, sometimes using part of your rent toward the price.

BTW, I am not disputing you, just playing devil's advocate and wanting someone to challenge my thinking. 

they are kidding themselves one needs to punch in 50% to 55% of gross cash flow for expenses then deduct your mortgage payments.. anything less than that will not play out over the years.

Also the strategy you are implementing plays a huge part with how to proceed.