I know it's zoned commercial but I will have to check with the city on what other restrictions might exist. 

I'll be looking for a 'hands off' brokerage if such a thing exists (while realizing I'll need a 'high level of supervision' my first two years) with a low fee structure for my own deals.

The abundance of 2-4 unit properties in Chicago just doesn't exist elsewhere.

BACKGROUND: Bought a property SUBJECT 2 an existing 1st lien (lets say serviced by Shellpoint) years ago.

And honestly I know that some people like you exist and you'll probably do fine with out an agent.

Probably needs more info - is there existing debt on the current rental property?

If I purchased the property outright with cash, stabilized it, then acquired my first loan (a DSCR loan), that wouldn't be refinancing right, as I wouldn't be replacing an existing loan?

1. use the 1031 money to buy 2 investment properties with a combined values >= the sales price2. use the 1031 money to improve one of my existing investment properties (e.g. building an ADU / remodeling)Thanks

Trying to go into an existing template and add/change variables is very tough.

If you have a high return on equity, then you are more likely to be making high revenue relative to your existing payment, which means you would be more able to cover the higher payment of a cash out refi and would then have cash to deploy.