For newspaper select The Record Reporter.

This allows you to make your sellers feel as though they are in an exclusive group of home owners that have the best homes on the block. often times you can lead with a very simple and honest, "I would like to add your home to the package of carefully selected properties to be sold to cash buyers, there's nothing you would need to commit to even if someone made an offer to buy it."

You'll usually need some sort of guarantor that will not declare bankruptcy the minute something goes wrong; too easy to do that in an LLC.Once you have a track record, private money folks will lend to you, and on larger properties (large MF) commercial real estate banking looks almost exclusively at the property.Spend some time researching the financing options.  

If there is a claim and you are insured that's a great first step...BUT, be very sure to review your policy and exclusions from Chicago.   

They focused exclusively on the value of the property.

If your looking to save money try People’s Trust its a different concept in HOI you have to use there contractors exclusively but premiums are super cheap about 1 quarter of what the other companies quoted me. https://peoplestrustinsurance.com/

This would mean not being able to claim depreciation, interest, etc.Alternatively, if you and your husband owned the property out-right, then this wouldn't be an issue.However, if it is done this way, your brother won't qualify for section 121 exclusion if the event the property increases in value significantly.Again, a lot of moving pieces.

Or is there a period of time required between using the capital gains exclusion?

DC is a huge market, so I am sure you will be able to find a meetup that focuses exclusively on MF.

Some banks hate working with brokers and some work exclusively with them.