I’d recommend getting a specific quote from an insurance broker for the property you are looking at so that you aren’t surprised.A 4-plex I own make a good example:  because of the combination of factors with it (age, flat roof, being a 4-plex) the insurance costs are 3x what any calculator predicts it should be (because most calculator tools use area averages based on the value of the home, instead of the actual home in all of its glory).

I'm sure you'll get a lot of "college doesn't matter" comments on here but if you're already doing it, I'd suggest either emphasis of or combination of Finance, Accounting, Marketing, Economics.

I was thinking to somehow acquire the property for next to nothing from the current owners who will likely get an insurance payout, use my connections with my old company and suppliers along with BP and other resources to demo (if not complete already) and rebuild with a combination of donated materials, money, time, and whatever paid services may be required. 

Don't underestimate techs companies ability to quickly copy each other for the best talent.The future I see for these tech companies/startups is a percentage of employees who are full time remote (20%), as well as more, smaller regional offices combined with HQ in a mega city.

Then you want to study the trends in the area and use a combination of commercial agent for more units, residential investor-friendly agent for 4-plex and less, and experienced large-scale wholesalers.

With a combination of luck and hard work i was able to partner up with one of the biggest apartment brokers in the midwest.

With a combination of luck and hard work i was able to partner up with one of the biggest apartment brokers in the midwest, and join a commercial firm. 

We’re thinking about asking to combine all of them for hopefully around $300k.

Also, your expenses look a little thin:I like 8% Vacancy for MFR, this is super local, though.15% combined for Repairs and CapEx.10-12% for good Management, unless you already have a bunch of units under management.What about water/sewer, lawn care, pest control, and admin/professional fees?

Total size of combined lot is 14,900 sq ft.