They updated zoning to 60' wide road required and you cannot do a private road and the lot only has 50' of frontage (its like state of oklahoma, narrow at street and opens up behind other home).There is no common sense and these long term politicians not only cannot think outside the box, but just do whatever they are told from the person greasing their pockets.  

Time is your biggest advantage right now.A few high-level points first:• Two years of runway is plenty• House hacking is the right instinct• Starting with secured credit is fine, you’re early• You do not need to rush into anything fancyNow to your questions.What type of property to focus onFor a first deal, especially a house hack, keep it boring and finance-friendly:• 2–4 unit small multifamily (duplex, triplex, fourplex)• Simple layouts, similar unit sizes• Something that qualifies for owner-occupied financing (FHA or conventional)This gives you:• Low down payment• Rental income offsetting your housing cost• A built-in learning experienceSingle-family can work, but small multifamily teaches you faster.Chicago-specific thinking (general, not neighborhood calls)Instead of asking “good vs bad areas,” focus on:• Areas with stable rents, not speculative appreciation• Neighborhoods where duplexes and small multis are common• Places with working-class demand and long-term rentersAvoid:• Heavy rehab projects for your first deal• Areas that only work if appreciation bails you out• Deals that rely on perfect executionYou want boring and durable, not exciting.LLC for your first purchaseShort answer: no, not for your first house hack.• Buy in your personal name• Use owner-occupied financing• Get the best rate and lowest down paymentYou can always move properties into an LLC later once you scale.

This can materially alter opex compared to a multi-family building that requires snow removal, common area cleaning & utilities, pest service and other misc. opex items that may not apply to SFH'sThen there's the reliance on self-reported data from individual investors, many of whom self-perform work, defer maintenance, or ignore routine capex items that prudent real estate operators treat as ordinary annual expenses.

A mentor can save you from a lot of the trial and error that new investors usually go through, especially with SFRs, rehabs, and choosing the right type of project.Curious what you’re looking for help with first like finding deals, running numbers, or figuring out the right strategy to start with?

While this isn't common, it still does happen. 

Quote from @James McGovern: @Kevin Sobilo I agree that what you have stated is common.

It's not common practice here in Chicago for a landlord to pay for gas. 

If you commonly find yourself without enough capital it could be that you're over-budgeting renovation costs and pricing yourself out of the deal. 

Congratulations Katy from Stockton, California on starting your real estate investing journey.Your story is so very common about living pay check to pay check and you believe investing in real estate will help you achieve your financial goals.You have about $50,000 to work with and wonder where to get started.Your grandfather became wealthy investing in commercial real estate developments and you believe this is also the path for you.Because you want to maximize the growth of your initial investment and minimize any downside risk, I would consider buying a value-add duplex for around $135,000.

But that is because I did lots of due diligence on the area I was investing in and allowed for a margin of error on the deal.