There's a big swing here in insurance and tax calculations I see and getting those numbers accurate are critical for your ability to not miss on good deals

For me, the first pass at underwriting is simply about determining if a deal is worth exploring further.In the current market, I’d say 9 out of 10 deals are dead on arrival.

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.

Have them pay a week or two before they arrive when they are past your cancellation period.

The S8 portion will very likely arrive like clockwork on the 1st of the month.One strong motivation for the tenant to pay is they lose their voucher if they are evicted or leave owing you a balance.

Such deductions could result in substantial refunds, providing critical financial support during a challenging time.Residents may also explore disaster loans or grants offered by the Small Business Administration (SBA) to cover damages or losses.

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.

The buyers had invested a lot into the deal (~$100M) and purchasing the property was critical to complete their development.

Local market knowledge is absolutely critical, and it helps to work with someone who really understands the landscape and its nuances.As others have mentioned, it’s a broad question that’s tough to answer succinctly, but I hope this provides some clarity!

Friendship and business don’t always mix well, so it’s critical to use a solid lease and treat this as a business arrangement.