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?

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

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

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

Does that number include tax, insurance? 

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.

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. 

Did you know that the tax code offers many incentives for real estate property owners that have a cost segregation study performed, thus allocating costs to 1245 property?

I know there are pros and cons to selling my primary home to my LLC but my question really goes a little deeper than just tax benefits:I am curious to know if I sell my primary home to my LLC regardless of tax benefits; and then rent it back to myself (through another LLC) … technically I don’t have a primary residence anymore so I could buy a Multifamily or Apartment complex as long as I am willing to live in one of the units correct?