You need to define what your goal is. 

I am working with the seller to accurately define property lines, easements, etc.

In addition to your online component, I'd recommend getting out to local real estate meetups and meeting others in your area who would be interested in working with you.

If I could expand on defining the strategy more I would take what you have already begun and just add to what's been said here in the following format:1.

Here are some code excerpts:31-17-1 (M) "Primary mortgage loan" means any loan primarily for personal, family or household use that is secured by a mortgage, deed of trust or other equivalent consensual security interest on a dwelling as defined in Section 103(w) of the Truth in Lending Act or residential real estate upon which is constructed or intended to be constructed a dwelling;31-17-8(M)(4)(4) Require the borrower to pay, in addition to any periodic interest, combined fees, compensation or points of any kind to the lender and broker to arrange, originate, evaluate, maintain or service a loan secured by any encumbrance on residential property that exceed, in the aggregate, six percent of the loan amount financed, including any yield spread premium paid by the lender to the broker: Provided, That reasonable closing costs, as defined in section one hundred two, article one, chapter forty-six-a of this code, payable to unrelated third parties may not be included within this limitation: Provided, however, That no yield spread premium is permitted for any loan for which the annual percentage rate exceeds eighteen percent per year on the unpaid balance of the amount financed: Provided further, That if no yield spread premium is charged, the aggregate of fees, compensation or points can be no greater than five percent of the loan amount financed.

There are lots of components when pulling together a successful deal.Personally, I believe that your first deal should be solid and relatively straightforward.

"Good investment" and "sustainable" (depending on how you define that) probably don't go together.Up-front cost, value proposition, and factors that aren't under the control of the owner.

Since you're already in Naperville, I assume you'll be able to find the time to get around meet local RE folks and pound the pavement to find deals.That said, from my own perspective IL/Chicago have some serious challenges over the next RE cycle (or two) that in my opinion make it imperative to have well-defined exit strategy before entering any new deal.

Has anyone tried house hacking while also employing components of the BRRRR strategy?

Given the totality of what you posted, you probably need the "tip" income from your job to "count," which will indeed only be counted after it appears on a couple years of tax returns.The base salary component of your income can be counted right away provided you work full time, with the college transcripts potentially serving to satisfy 2 year work history requirement, but that tip/bonus/overtime/whatever component needs to be on a couple years of tax returns.