This has significantly reduced the cash flow across both portfolios.

If you use Podio as it's designed to be used, it will streamline every thing you do--from managing leads, managing projects, reducing your internal email count, to making your internal communications more efficient because conversations (which otherwise might happen in email) happen "in context" -- of the client record in your CRM, the project, or whatever it is that you are discussing.  

Because this is the business we've built together, we enjoy working together, we each have roles that reduce the work load on the group and personally I like that the risk is spread out.

However, these costs can often be added to your property's basis, which helps reduce capital gains tax when you sell the home.Once the property is officially a short-term rental, subsequent repairs and maintenance would likely qualify as deductible expenses. 

Our business plan actually includes rehabbing distressed properties and conducting off-market transactions with owners currently occupying distressed properties using equity to reduce the out of pocket costs for the seller/buyer and to simplify the process.

Always have an exit strategy in case refinancing takes longer than expected, such as optimizing rents or reducing expenses.

Is there any creative way to avoid/reduce capital gains tax on the sale ?

I can’t make someone sell their property, some people will not be reduced to a dollar amount.

Or else reduce enough on price to deal with an eviction from an illegal unit.I don't know Chicago laws, but in NYC if you have an illegal unit, the tenant occupying it seems to have more rights than the owner does and doesn't have to pay rent... 

You will likely need to sit on the unit for a long time or reduce initial rent below the market for that unit to rent during the Winter. account for this by either offering a Winter special that will increase to market in the Spring or doing a short lease that ends in the Summer.