i'd pick a market close by, or that you have a personal connection to, or that you visit often.chasing cash flow by itself can lead to negative outcomes - for example, these investors bought in supposed "cash flow" markets:https://www.biggerpockets.com/forums/12/topics/1215726-break...https://www.biggerpockets.com/forums/963/topics/1195280-expe...https://www.biggerpockets.com/forums/48/topics/1137397-balti...hope this helps.

If you buy the single now your DTI will be negatively affected for future properties.

Make sure you budget for the negative year.

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.

Buying a portfolio might lead you to making decisions you don't have the experience and foresight to make well.

May negative cashflow until fixed.3) Buy established business: assuming you mean something other than real estate related.

Identifying neighborhoods with good schools, infrastructure, and amenities can lead to finding a hidden gem.Myth 4: It Is Only Seasoned Investors Who Can Handle Distressed PropertiesExperience is helpful in real estate, but you do not need to be a seasoned investor to do well in distressed properties.

They need a well-designed workspace, ultra-fast Wi-Fi, and long-stay conveniences like a washer/dryer and a fully equipped kitchen.Why This Matters for Your ROI:When your STR feels tailor-made for a specific type of guest, it stands out in a crowded market—leading to higher occupancy, better reviews, and repeat bookings. 

So eventually this negative cash flow property becomes cash flow positive and pays for itself including property taxes, hoa, mortgage etc.Trying to calculate how bad is my investment here or should i sell out if there is appreciation 

Keeping in touch with people in the field might help you keep updated and perhaps lead to profitable collaborations.By thoroughly researching, budgeting wisely, and managing your projects carefully, you can successfully flip houses even in a new state.