All Forum Posts by: Jarret Jarvis

Hi Gal,

Welcome to real estate investing! Starting local is often a smart first move — it gives you hands-on experience and better control. For market analysis, start with population trends, job growth, rental demand, and neighborhood comps. Out-of-state can work too, but only if you have a great property manager and understand the local market well.

Happy to chat more as you explore! #LETSGO

Hey Sarah — welcome to the REI world, and congrats on setting such a clear goal while balancing so much already! 👏

You're asking all the right questions. Investing locally for your first deal definitely makes sense, especially since you already have your core four (realtor, contractor, etc.) in place. That local team support is huge, especially when juggling W2 jobs and a growing family.

While out-of-state can offer better cash flow on paper, it comes with more moving parts and less control—which can be stressful for a first-time investor. Starting local gives you hands-on experience, helps you learn the ropes, and builds your confidence. Plus, suburbs like Elmhurst have strong fundamentals and are great for flipping or long-term appreciation plays.

As for STRs, make sure to double-check local ordinances—some suburbs are cracking down. You might also explore medium-term rentals (30+ day furnished), which are often less regulated but still highly profitable near hospitals, corporate hubs, etc.

Keep learning, stay flexible, and know that the perfect time rarely shows up. You’re already ahead by being thoughtful and intentional.

Are you leaning more toward a flip, STR, or long-term rental as your first move? #letsgo Jarret

Hey Adam — congrats on the Bucktown condo, that skyline view sounds incredible!

In terms of ROI, adding a roof deck could absolutely add value — both for resale and rental down the line. For rentals, you might see a 10–20% premium on rent if the deck is well designed and adds usable space. In Bucktown especially, outdoor space with a view is a huge bonus for tenants.

Since you plan to rent in a few years, the beauty is you get to enjoy it now and let it work for you later. Just make sure any work is permitted and HOA-approved (if applicable). Also, consider some low-maintenance materials so it holds up well over time.

Have you started looking into rough cost estimates or design ideas yet? #letsgo Jarret

Hey Sarah—welcome and congrats on taking the first steps (and on baby #2!). With your core 4 already in place, investing locally makes a ton of sense—especially for your first deal. Elmhurst and nearby suburbs still offer solid potential, even if STRs are tricky due to local rules. A flip or mid-term rental could be a great way to get started.

Out-of-state can offer better ROI, but it's a steeper learning curve—local is often smoother when juggling W2s and family. Happy to chat anytime if you want to dig into local options! #letsgo - Jarret

Hey Diana, great question—and it's awesome that you're thinking ahead about both rental potential and personal use. I've worked with several buyers in similar situations here in Chicago. Even when paying cash and having a clear idea of what you want, a good agent can still add value by spotting issues in the condo docs, HOA financials, rental restrictions, and overall investment potential (especially with how common assessments and reserves can make or break cash flow here). That said, it's all about finding someone who actually brings that investor lens—not just unlocking doors.

If you're doing a lot yourself, you might also be able to negotiate commission terms depending on the agent and situation. I’m happy to chat if you want to compare notes or get a second opinion on anything. Best of luck either way! #letsgo - Jarret 

Hey Sarah, sounds like you've been through the wringer—huge props for making it through that eviction and coming out with equity. That's no small feat. Given your goals, it might make sense to look into landlord-friendly states with lower barriers to entry and stronger cash flow potential. Markets like Indianapolis, Cleveland, parts of Alabama, and even areas in Florida and Texas have solid ROI and Section 8 demand. I personally invest in Chicago but also work with a lot of out-of-state investors and would be happy to share insights on what's working (and not working) for them. Feel free to DM me if you want to dive deeper! #letsgo

Hey Havan, welcome to the community and congrats on getting your first rental! That’s a big step. I’m based in Chicago and actively working in the southwest suburbs as well—happy to connect and share resources, local contacts, and insights on lending and deal flow. Shoot me a DM and let’s set up a time to chat!

Hey Lucas,

Love the way you're thinking this through—duplexing down in a 3-flat can definitely be a great house hack strategy and a smart value-add play. I’m a real estate agent and investor here in Chicago and have seen quite a few folks go the route you’re describing.

You're right to be thinking about permits and the potential scope of work. Even if you're not digging down again, you may still run into:

• Waterproofing requirements

• Egress window additions for bedrooms

• Upgraded electrical and plumbing (especially if existing lines aren’t to code or can't handle the added load)

• Possibly needing to sprinkle the building depending on layout and occupancy

As for financing, a Homestyle loan or FHA 203k could potentially work, especially if you're occupying the building. Definitely worth running it by a renovation loan lender early—they’ll help you gauge feasibility and get a rough idea of what’s financeable.

Also smart to be thinking about ARV—duplex-downs in the right neighborhoods can really boost resale value, but the premium depends heavily on finishes and layout.

If you want to connect offline or want intros to a few lenders or contractors familiar with this route, happy to help! #letsgo

Best,

Jarret Jarvis

Hey Michele message me when you get a chance but, an amazing loan program that associated bank used to have was this! I used it in 2020 and it was incredible for buying a multi unit with no PMI https://mortgageone.com/wp-content/uploads/2018/02/Associate...

Hey Jaclyn – welcome! Love that you’re combining your passion for real estate with the goal of more time freedom for your family—that’s the dream! I'm based in Chicago and work with investors all over the city and suburbs, especially on multi-family, fix and flip, and house hacking projects.

Would definitely be open to chatting deals, sharing resources, or just connecting to swap lessons learned along the way. Let’s keep the conversation going and see how we can collaborate! 👏 #LETSGO