While the cost can vary depending on the scope, zoning, and materials, I’ve seen similar projects run anywhere from $50,000 to $150,000, depending on factors like plumbing, electrical upgrades, and structural work.If you’d like, I can connect you with a few contractors or architects in Chicago who specialize in basement conversions.

We have an investor running a special next month on 10% down second homes where the cost is 3-4 points cheaper than it would be, on a normal Fannie/Freddie loan. 

A good attorney specializing in real estate can help draft these.3.

What value is expected or provided by an agent who specializes in multi-family residential, not commercial. 1-4 units.

They provide significant discounts for Bigger Pockets members.

Can anyone recommend hard money lenders who specialize in working with first-time investors?

There are lenders that "specialize" a bit more into those kind of areas, but from the eyes of a lender, what could happen is that they see 'rural' as a sign that you might struggle finding tenants down the road.

@Brandon Stelling I would recommend reaching out and connecting with various commercial brokers who specialize in each of these spaces.

We have worked in many areas of FL for years and specialize specifically in REI. 

If they sell them on amazon, they likely don't require any special handling.