Negotiating favorable terms is both an art and a science, and in real estate, it's a critical skill that can make or break a deal.

To me, that is extremely critical.

I’ve had to widen my search radius to smaller suburbs or target properties needing light cosmetic work to make the numbers work.Value-add opportunities: Adding amenities tenants love, like finished basements or upgraded kitchens, seems to justify rent premiums in this market.Navigating the competition:Be creative with financing: Seller financing or partnering with other investors has been helpful to secure deals when conventional offers didn’t cut it.Work with local agents and wholesalers: They often have their finger on the pulse of off-market opportunities, which is critical in a hot market.For those new to suburban Chicago investing, I’d say the key is finding the “sweet spot” neighborhoods—ones on the rise but not yet maxed out in price.

It’s a great reminder to trust your own due diligence and not let others make critical decisions for you, like hiring a property manager.For future investments, building a trusted team and maintaining direct oversight is key, even with remote deals.

With your background in lease management and site selection, that could be a natural next step.Regarding STRs, I can understand the hesitation—accurate expense tracking is critical, and not having that data can make evaluating deals frustrating.

Companies like State Farm, Allstate, or Chubb often come up in conversations, but comparing quotes with independent brokers might give you the best value.Since you're in a general partnership, it”s critical to clearly define liability exposure.

The later is critical to protect your investment.

Keeping contemporaneous records is critical.

Folks very often dont  realize the cost of being self employed when every facet of your life comes out of your pocket.

This is critical for protecting yourself, your property, and your neighborhood.Here’s why:Safety Concerns:Skipping checks could allow someone with a serious criminal history—like a sex offender or violent felon—into your property.