This might entail buying a single-family home with rental potential and living in one area while renting out the other units, or it could entail buying a multifamily property and living in one apartment while renting out the others.Financing Options: Look into traditional mortgages, FHA loans (for home hacking), and other inventive financing techniques.

I hope all is well.We have a STR in the town next to Ludlow and we were booked solid for the Winter (every single weekend and many weekday nights.)Check out our property "Honeypot Farmhouse" here.We're just coming out of "Mud Season" now where everything shuts down (restaurants, etc), but entering the Spring and Summer, we expect the rentals to pick up nicely.

Full rehab of the home to include new primary and secondary bathrooms, installation of new island and coffee nook with granite countertops, new water resistant LVP floors throughout, new paint, crown moulding in living room & kitchen, new electric water heater, and conversion of coat closet to mud room.

OR I become the only traditional residental lot and it changes absolutely nothing and my land value growth is still significantly capped because it will always be surrounded by MH zone, or stagnate until someone can buy out the whole area like has happened recently in other nearby areas in the city.

You certainly want to be on traditional booking channels such as Airbnb, Booking.com & VRBO.

Not sure that is a true statement about 2-3-4plex cash flowing vs single family with traditional investor financing. 

You get paid monthly and have NONE of the traditional landlord responsibilities. 

When bringing up subject-to as an option, the agent kept stating that his loan was un-assumable and that there was nothing more outside of traditional financing that could be done.

Buying my second home with traditional lending was my first step into real estate investing.

The kind of thing you only really see in America today in families with trauma and mental-health issues, traditionally where the pop refuses to get help and the mom refuses to stop enabling him.