Jim — with $280–500k to deploy and a preference for newer 4-bedroom homes, I’d focus on maximizing cash flow while minimizing future rehab headaches.

With about $100k to deploy, you’re actually in a strong position to pick up a solid rental and get your first deal done this year once you lock in the right team and market.

Once capital is deployed and timelines are set, correcting course costs more.Professional investors don’t eliminate execution risk — they plan for it.

Let’s move deals and create opportunities.If you have a creative financing strategy that you are looking to deploy in the Chicago market, feel free to reach out.

You buy, rehab in 3-6 months, sell, and deploy that capital again.

That "best case $200-300/mo positive" could easily become negative cash flow with one insurance renewal.Here's the framework I'd use: What's the opportunity cost of keeping $22k+ tied up in a break-even property for 5-10 years versus deploying that capital into a deal that actually cash flows from day one?

It's your total capital deployment across multiple deals.

Trevor, since you're asking about maximum ROI, let me actually run the numbers on both scenarios so you can compare apples to apples.Quadplex House Hack:- Purchase price: $350k (midpoint of your range)- Down payment (5%): $17,500 + ~$10k closing = $27,500 total capital deployed- While living there: you're essentially living for free or near-free (huge savings vs paying rent elsewhere)- After moving out (~1 year): ~$1k/month cashflow = $12k/year- Cash-on-cash ROI: $12,000 / $27,500 = ~43% annually- Plus you're building equity and getting appreciationBRRRR scenario:- Purchase: $120k property, hard money at 20% down = $24k + rehab costs- Here's where it gets tricky: rehab on a $120k property could easily run $15-30k, especially if you're hiring it out.

That's meaningful liquidity without killing flow, plus you get to consolidate into one payment and shift title to an LLC for better protection—no more personal name on the deed.Breaking down the trade-offs honestly:Pros that stand out:Asset protection upgrade — vesting in LLC shields your personal stuff from lawsuits/creditors tied to the property.Cash extraction — $20-30k to deploy on the next deal, emergency fund, or whatever.

That's way better than using capital to reduce debt when debt is cheap and assets produce income.The real play here is clear: Keep 0-12k in reserves (do this first), pay off 5-18k of the LOC to get breathing room, then deploy the remaining 2-15k into a down payment on the second property.