You should take a break from buying if the deals don't match your buy box, you are out of money, or for several other reasons (partner isn't on board, over-leveraged on different properties, acting out of FOMO, etc.).

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

If millenial homeowners can't even change their home's air filters, or snake a toilet, or change the oil in their car, that's guaranteed future business for HVAC companies, plumbers, mechanics, and those places all need a place to conduct business in.The commercial mortgage pricing software I use has somewhere around 50 different asset classes in it.

We have fair landlord-tenant laws, similar to Texas, but still the specific process is different.

Somehow they bury bad reviews on google with great reviews.For clarity, I own DealMachine (not batchleads... totally different companies).

A friend and I created one recently:https://drive.google.com/file/...It was meant to compare costs between different lenders, but you can use it to just see costs from one lender as well.

Would it make more sense to move the money we make from selling to a different property that could potentially increase our cash flow? 

Understand the fees involved and calculate the total cost for an entire year of management so you can compare the different managers.

The valuation and market value of a multi family property differs from a single family and you want someone that understands the distinctions if you go that route.

I still have a sizable rental portfolio but have been investing in real estate syndications in a multitude of different operators.