I think the big picture of your plan is definitely doable, although I would say financing might be your biggest obstacle.

No Business License is needed unless your municipality requires one in WI, you can fly as a sole proprietor, LLC, LP or Corp. biggest thing to watch out for is being identified as a business at your home, the municipality wants to nail you with personal property tax.    

Somewhere with some kind of yard is desirable as we have two dogs.The biggest thing for us however is to have a small carriage house or a guest house or something convertible into a rentable/livable space.I like north county a lot does anyone have some good recommendations to start searching for something like this to buy in that area.

My biggest hurtle with moving quickly is that most buyers are using FHA and I can't sell them the house in the first 3 months, even if I have it on the market in 3 weeks.

My biggest concern is the construction cost as my wife doesn't want to take out any more loans.

Investors at the end of their growth usually have all the income they desire so the dead cash is irrelevant.Your biggest problem may be actually getting the cash out if it is spread across 30 properties.Ideally you refinance at 5% and buy more income properties with minimum DB.

It turns out that at the biggest school nearby, someone built a massive apartment complex for college students right next to campus which is popular among students for living off campus.

That will go fast.My biggest concern with the property is it's a triple without the advantages.

My biggest concern is making my first investment a successful one.

It's just a matter of gaining the appropriate knowledge (for me, the biggest thing is knowing financing & how to use it best) and then actually DOING it, which most people never do.Now, I've gotten the real estate bug and can see all the possibilities (& how your home is actually a liability).