In your experience, do you find that it's possible to cashflow or at least break even with these properties and today's prices/rates?

My education background is in computer science, mathematics and some corporate finance, as well as have some internship experience in the quantitative finance space.

Others have little/no experience and will give you bad advice that takes you down the wrong path.I recommend you focus on educating yourself while saving more money. 

This is especially helpful since your goal is to replace your income and invest full-time.Market Timing: Bend, OR, has seen strong appreciation, but if you believe the market is peaking or stabilizing, now might be a strategic time to cash out.Cons:Losing the Low-Interest Loan: Your 3.1% rate is a huge advantage in today’s environment.

Quote from @Noel Coleman: I walked a property today for a flip with a contractor who I really liked and he seemed like he is really knowledgeable.

Without evidence, it's hard to say.First, you should educate all of your tenants to report excessive noise to the police.

If you’re using leverage, be extra cautious with your underwriting to ensure the deal still works at today’s rates.Economic Uncertainty: Inflation, potential recessions, or shifts in demand could affect rents, vacancy rates, and property values in some markets.Increased Operating Costs: Rising insurance premiums, property taxes, and maintenance costs can cut into profit margins, particularly for buy-and-hold investments.Regulatory Risks: Some areas are increasing restrictions on landlords, particularly short-term rentals.

Thank you for the absolute TREASURE trove of knowledge and selfless peer education provided on this forum. 

You can shift your perspective to enjoy what you're doing, yet reap the long term rewards by planting the seeds today. 

Quote from @Timothy Lawrence: Hello All,Today is the day I decided to upgrade myself from being a lurker to being an actual poster.