Or you can pay someone, like myself, who does architectural drafting to do the drawings.

David Greene has talked about this a little bit when he says 'portfolio architecture' but he's talking about the composition of a portfolio so slightly different. 

Asphalt (3-Tab or Architectural)?

architecture for someone who plans to invest aggressively in real estate, specifically 2-4 unit MF properties, and possibly commercial 5+ deals in the future.Should I just manage a healthy umbrella policy and forgo the entities entirely?

Well besides the hard costs (construction, materials) and soft costs (permitting, architecture, fees, engineering) people often forget holding costs. 

A little bit about me, I lived in a small town near the greater Boston area for the past 10 years and had just moved to O'ahu to pursue my Masters in Architecture, (but that's kind of on hold right now due to complication of the program...).

Now in most cases the same renovation will require an engineer report, and full architectural drawings….I recently had to obtain structural drawings and complete special inspections for a rear trex deck….Just a few examples of costs someone will incur flipping a house in Philly.

Upon entering, you are greeted by the soaring ceilings, a set of winding stairs that mirror each other & marble flooring that offers you your reflection, all working together to draw you into the experience of breathtaking views while you delight in the detailed architecture.

We produce architectural as-built floor plans and packages, which you’ll need to kick start this entire process.

Which reminds me....I know Worcester is smaller but if you're adding legal living space they may want a survey of the lot, architectural plans for the added space, don't forget about permit fees and other things that will hit your wallet.