You must check zoning to see if it's permitted in that area.

switch the zoning or rezone to hotel or a permitted grandfathered zoning instead of looking for the license go bigger and get it permanent not just one unit. loophole but very powerful how a lot of condo development is moving forward in miami they are hotels technically 

Get out of your comfort zone.

Duplex have different zoning that may permit additional units.

Get out of your comfort zone.

Get out of your comfort zone.

Get out of your comfort zone.

Lastly, cities/towns that have well thought out city planning and/or strict zoning if combined with the aforementioned characteristics will almost always lead to supply pressures that work in your favor. 

A Self-Certified permit review would likely only take a few weeks; as compared to 4-6 Months for a project which is not "Self-Certified" and needs to go through the "Standard Plan Review" process.A Zoning analysis should be performed for your property ASAP using a Plat of Survey to ensure you would be allowed to build what you want to build, and check for any potential "Setback" concerns when it comes to adding Dormers...

@Steve BergeronSteve,We're getting ready to develop a piece of high density zoned property as well.