If he owes a decent amount on the property, wouldnt the conventional route make him lose whatever interest rate he has?

You need to review your lease. tenant may be responsible for interior, but common areas and building facade should be LL.what is the current rate?

Contractors, unless you have a working relationship with them, normally do not want you bouncing ideas off them.Understand what their hourly rate is, have a discussion with them that you are okay with paying them an hourly rate if they walk the property with you and provide you a scope of work along with an explanation of what you can/can't get away with in regards to improvements.ask them if you go with them, if they can credit you the amount that you paid.Once you develop a working relationship with a few contractors, you can bounce ideas off them and expect quality responses.I do not invest in New York.Best of luck. 

Good occupancy and solid CAP rate.

If you own this as a rental then there is not homestead exemption and you'll pay much higher tax rate than a resident/owner occupant in SC. 

You can then rent at market rate but have to register it with the town annually and abide by their annual inflation rules.

There are short-term rental management companies that can help with that.One that I work with in Michigan covers the entire state and can advise on local short-term rental regulations or regulations that may be on the way, they can give you an analysis of the demand for short-term rentals in that area, nightly rates in that area, monthly occupancy percentage, and projected monthly income.They also let you choose the level of service you would like from them from full service to minimal.To your success!

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

Quote from @Vikas Jain: Yes, I have already seen the buy-in, im less concerned about that part of it, but just want to make sure its legitimate (plenty of opportunities where buyin is high but it doesn't always mean the product is good, just been burned in the past by others so trying to do better due diligence this time around)Their success rate, as of now, is 100 percent.

I've had smooth loans close with Kiavi and I've had rough ones, same with Roc.When Loans start to be troublesome:1) The borrowing entity docs are a mess2) The appraisal numbers are lower than expected3) Messy background reports4) Loans happening in an environment where market/rate fluctuating unpredictably 5) Your loan officer and their team are poor at their job6) Title issues that depend on county docs, that can be slow and painfulThere's more but it's Friday and I'm tired....