I would suggest you hire an inspector as well as have a general contractor go out to the property.

The contractor we hired renovated several other units in the same building and did a beautiful job.

Our goal is to be able to use either some type of software or spreadsheets to continue to build off of and help dial in our costs as we begin to hire more contractors for our team.

If you grow quickly or get too busy, you’ll have the funds in place to offload management without stress.5.Hire specialists, not “do-it-all” handymen.

Your first hire is unlikely to work out though, was you won't have a good hiring system in place. - So, recommend having that first hire document the crap out of what you want them to do.

Hired hourly handyman and friends to assist me in upgrades of windows, door, cabinets, basically all new fixtures in 12/2009.

There is virtually no reason to keep “cash” on hand for repairs. 

Lenders typically require a resume for the GC involved in the borrower's project to assess their qualifications.When it comes to a GC getting funding for their own projects, while some lenders will take your experience as a GC or builder into consideration, most primarily look at your track record as a borrower on title when determining approval and pricing.That said, if a lender deems your experience sufficient, they may allow you to act as the primary GC on your own project instead of requiring you to hire a more experienced GC. 

Hire a Licensed General Contractor (Best Path)Since you’re still getting your Michigan Builder’s License, you might have better luck partnering with a licensed contractor for loan approval.

Hire an accountant—but maybe not for $6,000/yearA real estate tax pro can help you save money, but $6K a year is way too much unless you own multiple properties.