There are several things to fear money loss on a bad investment, government involvement in RE, bad tenants that cost time and money, hidden maintenance issues and/or land issues and the list can go on.Today, I don't fear money loss or tenants,  the big unknown is how much the government wants to get involved in either taxes or landlord/tenant issues.

While you can have a checklist of income, credit score, criminal background, landlord reference, etc, to me the bigger tell of good versus less than good tenants came from all the interactions prior to leasing.  

It also gets you into real estate sooner and lets you start gaining experience as a landlord.

I am just looking for insight from local MA realtors, attorneys or landlords regarding what my typical monthly expenses (if any) will likely be (I don’t mean one-off expenses like roof repairs). 

@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.

I don't like seeing a bunch of blue haired nerds running around crying about how evil their landlord's are for forcing them to pay their rent on time, but I don't want being a blue haired nerd to become a criminal offense.

Best decision I've ever made. 4-6% average annual appreciation rate, stable job growth, population growth, drivable to the Bay Area, close to Lake Tahoe, no state income tax, 4th lowest property taxes in the Nation, much more landlord friendly than CA, land constrained meaning limited supply, etc. 

Summary: I’m currently working on a project to analyze rental market trends and help real estate investors, landlords, and property managers identify high-performing areas.

Scranton area seems to be a lot more landlord friendly than New York is, and the numbers seem better as well, Section 8 seems appealing for the guaranteed income but I will definitely take that information under consideration as I’m looking to invest in the area. 

. $40/month off works out much better for the tenant, even though they may not realize it, and it's a killer for the landlord