Does anyone have experience with the ADU program offered in Boston? I am looking into a basement conversion for a recently bought single family. Looking for advice in regards to planning, design, financing (Boston off...

At the two year mark, you will have fulfilled your owner occupied lender requirement and be eligible for capital gains exclusions by satisfying the residency requirements of 2 out of 5 years as your primary dwelling.  

This built instant equity in my home.

Gillermo,If you purchased a Homeowners Policy for the house, you will probably need to rewrite the coverage to a Dwelling Fire policy prior to renting it.  

William,If you have a Homeowners policy and the property is not owner occupied you will probably need to rewrite the policy to a Dwelling Fire (some companies may call it a Landlord policy). 

Yes you're probably right about speaking with another company and seeing what they have to say as it seems like one foundation or slab should cover all attachments to the dwelling.

The "repeat" aspect is the overall vision, not necessarily an instant jump.

A nonconforming use is a use of land, buildings, or structures that was lawfully established prior to the effective date of this ordinance, or any amendment thereto, but which does not conform to the regulations for the zoning classification in which it is located.Nonconforming uses may be continued subject to the following limitations:a) No nonconforming use shall be extended, expanded, enlarged, or moved to occupy a different or greater area of land, buildings or structures than was occupied by such use at the time it became nonconforming; provided, however, a nonconforming use may be extended throughout any parts of a building which were specifically designed and arranged for such use at the time it became nonconforming.b) No building or structure devoted to a nonconforming use shall be enlarged, extended, recon­structed, moved, or structurally altered unless such building or structure is thereafter devoted to a conforming use; provided, however, such building or structure may be enlarged or extended upon prior authorization from the Board of Adjustment, which authorization shall not be granted unless the Board of Adjustment makes each of the following findings of fact:1) The proposed enlargement or extension shall be de minimis in relation to the existing building or structure.2) The proposed enlargement or extension shall not increase the intensity of the nonconforming use, which is to say, it will not result in an increase in dwelling units for a residential use nor in gross floor area for a nonresidential use.3) The proposed enlargement or extension is designed so that it will not render the use of the property any less compatible than it is in its existing circumstances.4) The authorization of such proposed enlargement or extension is not otherwise contrary to the public health, safety or welfare.c) A nonconforming use of a structure may not be changed to another nonconforming use unless such change is authorized by the Board of Adjustment.

But for many locations, that's just not going to happen.I reckon your main investment goal should be to find deals/bargains that give you instant equity, even if you're then out of pocket each month. 

@John Tran this is residential multi-dwelling.