Ideally it would combine a CRM, calendar, timeline, etc. 

A few things to think about:21% combined for CapEx and Maintenance is pretty high.

At the same time, see if the lender will do a HELOC to allow you to tap into the additional equity you have.I also think you would be well served to underwrite a bit more conservatively. 10% combined for CapEx and Maintenance is low.

(I'm wary to believe that, due to other bad advice and mistakes on my return.)Also, I'd probably rather not aggregate the three properties, since based on that article:If a qualifying real estate professional makes the election to aggregate all rental activities for purposes of measuring material participation, the combined rental real estate activity is treated as a single activity for all purposes of Sec. 469, including the disposition rules of Sec. 469(g).

Is purchasing the property next door to combine my lots into 16k sqft total worth it?

As a lOKal yokel specific combination of Del City and section 8 makes me want to run for the hills (which if you’re familiar with our landscape means “a very long way”).I’m happy to add value in any and every way possible.  

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.