I would be cautious buying in the saturated areas because there are so many similarly sized properties that price is becoming increasingly the deciding factor. 

If Oak Park allows STRs, leveraging that history could make the property stand out.That said, unless the home has been preserved as a landmark or has unique historical features, the value boost may be more about novelty than a significant price increase.

Hi @Brendan Jones I moved to Nashville in late 2021 to begin my homeownership and investing career, buying a primary residence, house-hacking it, and transitioning to a long-term rental once I bought my next property (also in Nashville) so would be happy to share my experiences.There is a lot of interest in STRs in the Nashville Metro area, but the zoning has become increasingly strict over the years.

If this property is hard to rent, or is functionally obsolescent (only 1 bathroom, no yard, etc), or has deferred maintenance that will be costly, or is in a location that is not appealing to Tenants, then maybe a sale would be a good option in favor of a property that has better Tenant appeal, which will likely increase rent and avoid long vacancies in between Tenants.An option to consider....

Quote from @Paul Lucenti: Creative methods tend to increase risk.

In the City of Austin, we saw a 6.5% increase to $575,000*Total sales increased 2.5% in the metro.

However, note that claiming additional depreciation will increase, not decrease, depreciation recapture tax (up to 25%) when you sell.Key Considerations (Updated for 2025):1.

But ...The first thing I observed was the replacement cost portion of the quote, was, IMO, less than what it will actually cost to demolish the remains of the existing structure, pay for any hazardous waste removal following a catastrophic loss, and actually pay to replace the property in the event of a total loss, even though I used the quote feature to increase the replacement cost value by 20% (the maximum it would allow).

Not only for the census ending in 2020 but also the projected population from 2020 to 2025.I agree that population increase is important and should be factored in when analyzing a property. 

The deduction is optimized as values increase and can potentially offset the entire net investment (including down payment) for high wage earners.