Of course being a flip means I owe more than $300k in taxes so that bites.

Plus, since our guests stay for more than 30 days, we're not subject to the short term tourist tax & licensing.

If you- own a short term rental in your name- have a mortgage on that property - self manage Do you still create a LLC to manage your rental business or do you manage it under your name and then file income and expenses as part of your tax filing?

What's the best way to track your property income/expenses for tax purposes?

- How much should we expect to pay for taxes and insurance?

@Vikranth BiradarI recommend finding a tax strategist that specializes in real estate taxation, REPS and cost segregation.

High Maintenance Costs: Escalating maintenance costs can erode your profit margins.Change in Neighborhood Dynamics: Shifts in the neighborhood that negatively affect your property’s value are a red flag.Better Investment Opportunities: Selling might be wise if you've identified a more lucrative investment opportunity.Cash Flow Necessities: If you need liquidity, selling a property can provide a significant cash inflow.Tax Implications: Sometimes, selling can be advantageous for tax reasons, especially if you can benefit from capital gains tax laws.Personal Financial Changes: Changes in your personal financial situation may necessitate liquidating assets.Retirement Planning: Selling investment properties can be part of transitioning into retirement.Portfolio Diversification: Selling might be necessary to avoid overconcentration in real estate.Legal or Regulatory Changes: New laws or regulations can impact the attractiveness of holding onto a property.Ownership Challenges: If the burden of ownership outweighs the benefits, it may be time to sell.Real Estate Market Trends: Anticipating a downturn in the market can be a reason to sell early.Interest Rates: Rising interest rates can reduce the pool of potential buyers and lower property values.Property Value Appreciation: If your property has appreciated significantly, taking profits might be smart.Lifestyle Changes: Sometimes, personal life changes dictate a shift in investment strategies.ConclusionDeciding to sell an investment property is a complex decision influenced by market conditions, personal circumstances, and future investment goals.

Does that number include tax, insurance? 

I'm hoping to connect with a reliable CPA that I can build a relationship with to help me get on track with my tax returns but also someone that can provide sound advice as my business grows.

@Patrick Rafferty, Any tax paying entity can do a 1031 exchange.