Welcome, Eric  with your real estate background and boots-on-the-ground market knowledge, you're already steps ahead.

Having the right team on the ground makes these deals much smoother, especially if you’re buying from out of state.

At the same time, start building relationships with local agents and property managers who work with investors, as they’ll give you the on-the-ground perspective you can’t get online. 

For what it’s worth, I invest in Columbus, Ohio and have seen plenty of out-of-state investors run into similar issues—it’s a reminder of why landlord-friendly markets here in Ohio can still be really good if you’ve got the right boots on the ground.

Hey Aaron, I recommend planning a short trip to get boots on the ground.

Stairs & AccessYes, you can add interior stairs to connect the first floor and basement with a lockable door—lots of Chicago owners do this for duplex units.For a legal apartment, you’ll need a second point of egress from the basement to outside ground level per Chicago building code.If It Were My PropertyKeep the 2-flat zoning so you don’t lose tax benefits.Add interior stairs + side exit for flexibility.Frame off a mechanical/common area for panels, furnaces, and water heaters.Leave the basement unfinished until you’re ready for permits or rental use.Budget for separate utilities later if you want true rental independence.I hope this helps you a bit and I sent you a DM on BP and hopefully you're able to assist. 

So, do your homework, trust your people on the ground, which is going to be your Realtor and PM company, and don't jump into Ohio or any Midwest market just because the prices are lower than California.

Music keeps me grounded when the tech world gets too intense.

Evaluate Their Tools & Resources – Do they have HOT sheets, third-party revenue projections, ground support and comps — or just MLS links?

In Seattle, you have grounds to terminate if the tenant is late 4 times in one year.