If you're going with a traditional HML, your lack of experience is going to cause some out of pocket expenses for you.

Not a joke, but my dad(who is a real estate broker) always said, "I'm an expensive cab driver, if I take you to the right place, I'll get a big fare!"

- Based on your experience, what should we expect for maintenance expenses? 

For example, I have seen brand new homes for average market price or lower in Wendell with a fixed 5% rate.

For instance if he says $20,000 in repairs I’m not that worried and will offer close to where I figured I could offer based on income and expenses.

If possible I would want the amortization over 25-30 years.I know cash out refi is quite expensive with the origination fee and everything, early pay off could cost too or drive the rate up.

Also a more effective use of time, although definitely more expensive. 

Sounds really expensive and unnecessarily complicated.

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

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.