We still owe roughly $900K on a 3% mortgage.We’re planning to retire abroad and are weighing two options:1.Sell the home – I already have a buyer lined up, so this would be a straightforward exit.2.Rent it out long-term (furnished) – While I don’t think the rent will fully cover the mortgage, it might come close.

If one or more units are vacant, the remaining units often don’t provide enough cash flow to cover expenses, making it harder to meet operating costs.Maintenance costs: A fourplex comes with four times the appliances, plumbing, HVAC systems, and other components to maintain, leading to significantly higher repair and maintenance expenses than single-family homes.If you want to see the detailed calculation, read this BP blog - More Units Doesn’t Mean More Money—Why a Single-Family Home Can Beat a Fourplex.Resale value: Multi-family properties have a limited buyer pool—mainly investors—who base their offers on CAP rates.

I have a GC friend in PA trying to request 196k, as a “gap” to supplement whatever the HML cannot cover. 20% ROI, 6 months. 

Currently finalizing a deal for another property with a different individual investor where we will have the same payout model, but they will put up a bit more cash to cover all the admin work I have to do to set things up. 

Covering a significant portion of my mortgage has been a great reward.Solution: My four levels of vetting have helped me find quality room-renters over the last 18 months.I think you already have the answers to your situation.

Hi Owen- Most others have covered the specific areas to consider.

You can only play games for so long.Chances are your next door neighbor is an IRS agent and turns you in when your tenants blocks their drive or some other random event disturbing your IRS neighbor.ADU catches fire and your insurance won't cover you, because it was an illegal and unpermitted structure.The city inspector told the last guy not to build or rent it, and is now pissed and wants to make an example of you and just red tags the whole property and no one can occupy for the next 1-2-3 years while you wait for a hearing.Then when you get the hearing, "staff" recommends you tear the whole structure down, and if you still want an ADU, you can apply for a permit and rebuild it.Your tenant quits paying rent and won't move out and you can't evict them, because there is no valid lease and they're just your "roommate".Probably a dozen other bad things can happen to you when you do stuff like this. 

Home was nice 4 Bed 3Bth under $550K with a decent size lot/yard and it only required 5% down as a New primary.Now I am not sure how big of a home you need but as you can see $100K covers much more in a scenario like that one above. 

While Section 8 appears to promise "guaranteed" income, the reality is quite different.Section 8 typically covers about 80% of the rent with tenants responsible for the remaining 20%.

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).