My issue currently is more consistent income as I'm on commission percentages as an assistant and carrying a mortgage while I theoretically would wait for renters would drain my resources after rent/food/bills.

The flower bed had weeping holes for excess watering; the water would drain out and leak into the drainage system in the middle of the garden. 

I would avoid garbage disposal, because it just encourages putting food down the drain which, even through a disposal, will cause more plumbing issues over time.

In my experience drain stacks crack at turns, tees, and fittings.

If water came up through the drains, complain to the City of Chicago about poor/malfunctioning  sewers.If water came in due to collapsed/clogged drain pipes.

With little ones, they can drain you. 

There’s a cost to working a 9-5 that is taking away from doing something that can eventually make you a lot more money and more importantly not drain your energy.

Without positive cash flow it will only become a greater financial drain on your life.

I have a rowhouse style property in Washington, DC and the down spout for the back of the roof leads to a drain outside of the basement door.

You may need to install a drain outside or you could build up the surrounding area with some concrete to divert the water away.