This would allow you to defer the capital gains tax, and instead of taking a large tax hit, you would be able to use the tax to invest in a nicer property/properties.

It’s inexpensive to provide but can make a big impact.Comfortable Bedding: Investing in high-quality mattresses, pillows, and linens improves the guest experience and leads to better reviews, which can boost occupancy rates.Smart TV or Streaming Services: Offering Netflix, Hulu, or similar services is a low-cost way to enhance guest entertainment and stay competitive.Fully Stocked Kitchen: A well-equipped kitchen with basic appliances and utensils appeals to families and long-term guests, saving them money on dining out.Dedicated Workspace: If your property caters to remote workers, adding a small desk and ergonomic chair can set your listing apart.Outdoor Spaces: If your property allows, an outdoor seating area, fire pit, or hot tub can significantly increase your nightly rate and attract more bookings.Energy-Efficient Features: Guests appreciate eco-friendly options like LED lighting, smart thermostats, or solar panels, especially in eco-conscious markets.Keyless Entry: A smart lock is a relatively small investment but offers convenience and security, which many guests value.If you’re deciding on amenities to add, it’s always a good idea to research your local market.

- You can buy using FHA 203(k) loan which allows you to finance repairs into the purchase mortgage.If you find you like being a landlord, you can BRRRR a property every year.You can also start BRRRing rentals w/o planning to live in them.

Quote from @Alex Moazeni: You are making the common mistake of allowing a tenant to push you around.This is your property.

A cash-out refi could allow you to set aside some funds as a reserve or at least pay down your debts so that your lines of credit (credit cards etc) can act as your emergency reserve when more bad things happen. 

This way, if vacation rental management becomes too demanding or isn’t feasible, you have an alternative strategy in place.Make sure to confirm that the HOA or association allows rentals at all.

If it is good enough for my local building authority to get permitted, it is good enough for me.In both of these cases, it was the presence or absence of the all mighty built in closet that allowed me to execute these real estate maneuvers. 

But assume you found a property they would allow you to do it on. 

This is due to bonus depreciation which allows taxpayers to deduct 40% of qualifying property costs in the first year, in addition to regular depreciation for new construction and improvement.

Adding a washer/dryer to a $500,000 two-flat in Rogers Park could allow you to raise rents by $150/month, significantly boosting your ROI.8.