This has significantly reduced the cash flow across both portfolios.

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.

This change has helped generate more bookings, but it comes with a trade-off: guests booking single nights on Fridays or Saturdays might prevent full weekend bookings.Lowered PricesWe’re utilizing PriceLabs for dynamic pricing and have reduced our rates to stay competitive during the off-season.Listed on Furnished FinderWe created a Furnished Finder account to target mid-term stays, which I hoped would solve our slow-season problem.

That kind of experience builds confidence and reduces risk over time.