I do all of this remotely, so I use the above process to filter out 90% of the properties and then send the other 10% to my local team for verification.

I would prefer 4, but I have to make the numbers make sense for me and my current financial position.I attended a webinar last night from a veteran who's been in real estate for years and understands use of the VA loan.

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.

Consider connecting with local REI meetups, hospitality groups, or even online forums like this one to find like-minded investors.You could also pitch your successful track record to potential equity partners.

My only recommendation is you go with someone local to where you are.

Trustworthy property managers can make or break a portfolio, and I’ve found that vetting them carefully—checking their reviews, local reputation, and how they handle tenant retention—is crucial.

P.S; We live in Wilmington NC so both markets would be "long distance" P.S.P.S there are no reasonably priced multi family properties local to us.

If local sales support the new value then you should not have to deal with the seasoning requirement.

I have a local handyman that helped me hired junk removal company and pest control for the roaches.

You could also consider house hacking locally.