Look for a small/mid size local bank that specializes in this, they will detail what you need, survey, building permit, architectural plans and a builder contracted for starters.Or when you're ready to subdivide/redevelop you just sell to a builder and have them split the lots and transfer title to you for your smaller lot, he keeps the others and let him mess with the utilities and building. 

Assume 8% mortgage rate and 30-year term.

You did a great job on most of the details but it looks like the floor plan you started with is now the issue and is not really correctable.Looking at the Zillow map of the area, I see very few houses over $400K and most around you are about $100K+ under yours. 

There was a lot of information I didn't mention in this post since each company and individual can operate differently so if there was something I failed to mention, please feel free to leave a comment).The terms Hard Money Lender and Private Money Lender can be confusing because people sometimes use them to mean the same thing.

I know there are some restrictions on short term rentals (1 month min.) in the area but I believe even doing 1 month rentals at a minimum, the financials of the deal still work.

Part of your ability to excute includes your personal financials but I would wait until you are further along to provide that level of detail.

Hi Bigger Pockets Community,I live in Lincoln Square and am eager to invest in a multi-family property for a long-term hold - ideally on the northside.

They will probably accept the offer with that term.

Assume 8% mortgage rate and 30-year term.

There are schools all over, including Wilmington for sure. https://dpr.delaware.gov/ has all the details on schools and requirements, typically the schooling can be done online and then the test is done in person at a testing center.