@Tove Fox - Residential Real Estate InvestingPros:Lower Entry Costs: Easier to get started with less capital required.High Demand: People always need homes, making demand relatively stable.Easier Financing: Mortgages are generally easier to secure with favorable terms.Simplicity: Easier to understand and manage, especially for beginners.Flexibility: You can use it as a personal residence or rent it out.Cons:Tenant Turnover: More frequent turnover leads to vacancy and more management.Lower Cash Flow: Income potential can be modest compared to commercial properties.Emotional Buyers: Residential prices can be influenced by emotions, leading to price volatility.Maintenance Burden: Landlords often deal with repairs and maintenance, which can be time-consuming.Commercial Real Estate InvestingPros:Higher Income Potential: Stronger cash flow and higher returns are common.Long-Term Leases: Tenants often sign longer leases (3-10 years), reducing vacancy risk.Professional Tenants: Business tenants tend to take better care of the property.Valuation Based on Income: Prices are based on the income the property generates, not market emotions.Shared Costs: Tenants often cover property expenses like taxes, insurance, and maintenance (via triple-net leases).Cons:High Entry Costs: Requires more capital or partnerships to get started.Complex Management: More expertise is needed; you may need a professional property manager.Economic Sensitivity: Commercial properties are more sensitive to economic conditions.Challenging Financing: Securing financing can be harder, with stricter terms and higher interest rates.Zoning and Legalities: More complex regulations compared to residential properties.Key Differences:Risk: Residential tends to be lower risk, while commercial offers higher rewards but with greater risk.Management: Residential is easier for DIY investors, while commercial properties usually require a team.Scalability: Commercial properties are easier to scale, offering more potential for significant cash flow increases.

Prioritize properties with strong rental potential and set aside reserves to handle unexpected costs.Finally, familiarize yourself with tenant laws in your target market, especially in Portland, and consult a real estate-savvy CPA for tax efficiency and legal considerations.

But the answer for everyone may differ.Here are the personal attributes I see in those able to achieve a higher than market ROI, enough higher to be able to “scale”.1- Knowledge of real estate principles, real estate law and real estate finance2- Minimum 3 -5 years full time, or near full time experience directly related to real estate investing3- Ability to utilize technology for increased efficiency, capacity, and accuracy4- Excellent hired legal counsel and excellent hired marketing help5- Established method(s) of obtaining consistently high QUALITY deal flow6- Ability to manage and choose people who are NOT employees: Attorneys, Appraisers, Mortgage Brokers, Real Estate Brokers, Title Companies, Surveyors, Marketing Specialists, Accountants, Contractors, Consultants, Property Managers7- A VERIFIABLE track record of success8- Ability to identify, analyze, and negotiate a deal that can be “worked” for “enhanced” ROI9- Some type of competitive advantage; for example for me it’s my ability to analyze and identify mortgage loans that are actually less risky than all other lenders believe (on the investing in debt side), and on the real property side it’s my ability to analyze”pull the trigger” with LESS information than other investors need,  combined with the ability to pay cash, or raise significant capital almost instantly as well as being able to obtain loans at the lowest prime customer bank rate with no recourse or personal liability.  

I am in PA and yes, it is legal to charge late fees to your tenant regardless of Section 8 subsidies or not, provided the tenant's lease allows for them.

For example, I have my house, am building a legal JADU, but later down the road I decide to rent my entire house and buy another primary residence.

Has anyone had any luck obtaining legal counsel and fighting this?  

Your calculations should include utililies and repairs, legals, snow removal, etc.

They can and will fine you heavily and order you to remove it completely if you don't go to them first and ask for an inspection and do what they want to make it legal and permitted.Don't try to "get away with it".Be a businessman and fix the problem the right way.

At the same time, someone else reduces your debt, and you get to use the tax code to improve your tax situation legally.  

If this is a big-ticket item, you might consider legal action against Airbnb.