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.

A 1031 also adds complexity and timing pressure.Watch Out For:Opportunity Cost: Renovations tie up cash that could go toward other investments or reserves.MTR/STR Management: These models require more time and effort than LTR, even without a property manager.Market Risks: WA properties may appreciate slower than expected, and higher costs could reduce your margins.If cash flow is your priority, option 1 (renovate and STR/MTR) likely offers the highest upside.

Great tenant but property tax increases have reduced my cash flow.

We reduced the price already by a quarter and it's been posted since late August/.Any advice or experience in this would be appreciated.

It makes your house more attractive and reduces vacancy.

Yet for owners of rental SFRs, duplexes and condos—not to mention retail and restaurants—COVID-19 threatens to reduce landlords’ rental income, perhaps entirely.