The guest stay with discount and toilet replacement did not cover the cost of the unit for the stay. i have the issue on occasion that the guest is expecting a bigger unit and thinks the price is high but they do not realize the value of the unit.  

I don't plan on adding anymore and just putting my capital into my existing STR's. 

Because of this the supply is relatively low which means the ones that do exist tend to make good money, especially if you theme it toward bachelor/bachelorette parties.

If you’re looking to connect with private lenders, start by tapping into your existing network—friends, family, and colleagues can often be a great starting point.

The buyer would need to show solid financials also of course (good credit, experience operating rentals, proof of funds for down payment and adequate reserves to cover any unexpected cap ex).

You could also offer to cover part of their tax liability through negotiation or encourage them to convert the property into their primary residence to use the IRS exclusion for up to $250K/$500K in gains.

If it's way out of whack with the market average, dig deeper.Debt Service Coverage Ratio: Key for nderstanding if the property's cash flow will cover financing comfortably.Historical Vacancy Trends: Especially in areas like Chicago, where local job markets fluctuate, knowing vacancy trends can help you anticipate rough patches.Rent Growth vs.

You need sufficient rental income to cover your expenses, or you bleed money. 

Otherwise, you won't have the extra funds necessary to cover the rising costs of goods and services in the future.What causes rents (and prices) to increase?

Quote from @Lionel Quiambao:  ... and maybe throw in the option for the tenant for more speed at an increased rent to cover the additional payment.