Shed has collapsed roof.

Look for properties with updated roofs, electrical, and plumbing.

I am sorry that the storm that passed through just prior to your stay required emergency roof repairs. 

Albany, Syracuse, Utica, OH, PA, etc.) for cashflow.The challenge in these markets is that demand is through the roof, and many properties either sell at the asking price or above the asking price (Suffolk's sale price average was 1.5% ABOVE the asking price).If I were in your shoes, I'd explore local and remote multi-family options before considering the mid-term rental route.All the best!

I also like Haverhill as a peripheral city to Boston - commuter rail stop, close to major highways, and nice downtown with some municipal improvements on the way.PROPERTY OVERVIEW:Unit Mix: (3) 2BR units, (1) 1BR unit, plus parkingRecent Upgrades: New roof, updated electrical panels, new hot water heaterLocation: Walkable to downtown in a well-established neighborhoodParking: Dual driveways provide off-street parking for tenantsRENOVATION SCOPE & COSTS:Limited photos available, but if the rest of the house is in similar condition, likely cosmetic rehab only (~$30K per unit).Potential upgrades include paint, flooring, kitchen cabinets/counters, and appliances.Ideal for a DIY landlord or owner-occupant looking to add value, but also works well for any investor seeking cashflow.MARKET RENTS & INCOME POTENTIAL:Market Rent Estimates (based on local comps):2BR Units: $2,200 - $2,500/month1BR Unit: ~$2,000/monthTotal Potential Rent: ~$8,600/monthCurrently Fully Tenanted:Current rents cover mortgage payment.Would need to manage tenant move-outs before renovations, which could delay the project.Evictions may be necessary if tenants do not leave voluntarily.FINANCIALS & PROJECTED RETURNS:Financing Assumptions:20% down payment, 7% interest rate, 30-year fixed mortgagePrincipal & Interest (P&I): ~$4,524/monthAnnual Expenses (including taxes & insurance): ~$17,000Utility Costs:Heat is not separately metered, leading to higher utility costs (factored into analysis).Projected Cash Flow & Returns:10% cash-on-cash return once stabilized$31K+ annual cash flow5-year total ROI ~95%, factoring in principal paydown and 2% annual appreciation

It all cash flows like a gold mine until the roof needs to be replaced, the main line goes, or you get your first turnover bill and need to upgrade a kitchen. 

What happens if the roof has to be replaced?

Check out this site - https://theluxurypergola.com/blogs/louvered-roof-info/hurric...They cover wind resistant pergolas in general but I would make sure whatever you get will be able to stand up to hurricanes that happen there from time to time.

That may increase your cost or limit the coverage you can get.The Year that the following were updated (either partially or fully) would be good to know:- Heating systems- Roof- Plumbing- electricalSome companies will not write properties with systems that have not been updated.As long as you are living there, the proper policy for a 1-4 family is a "Homeowners" policy.

I am from Spokane Washington, and the real estate prices there are through the roof and make it almost impossible for a new investor to get started.