Tough to say in this case you gotta know everything down to the dollar and also assess both your skill levels of executing the rehab and then deal with the sale.

They will be removed (paid off) when you execute the Option the buy....and the "owner" owns the property 100% from the time the sale agreement is signed. 

I like to see a handyman on staff for all the little things to save money and they usually make a few dollars off having this luxury in house.

You will want to start with a cover letter then attach to a business plan that goes over at least the following:Mission Statement - including executive summary and financial overview.Business description - name and location of business, principal owners, legal structure, status and type, definition of products/services, major strengths and challenges, strategic goals and objectives.Operation Plan - location, physical facility, labor, suppliers.Market Analysis - industry trends, description of total market, target market, analysis of competition, production/services differentiation.Sales Strategy - Pricing policy, distribution, promotional efforts.Management Profile - personal history of key participants, duties and responsibilities of key participants, compensation, available resources.Financial Analysis - sartup costs, source and use of funds, capital equipment list, income statement projection, monthly cash flow projections and assumptions, balance sheet projections, personal financial statements, personal income tax returns.It all a numbers game - make sure you present your number truthfully and make sure you educate yourself on every aspect of the business.

As important as PM is, I actually think the people and process to estimate rehab costs and execute the rehab as the most critical.

If you got your own maintenance staff already, then that makes things easier. 

If you are getting antsy for a quote than get one from a more established company that has the staff to support getting quotes out fast.

Looking for some feedback on planned next steps and how best to execute on them.I currently have 2 rental properties and am looking to acquire a third through the HomeReady plan in Chicago as my first house-hack and first multifamily (2-3 flat).

I feel like I'm missing something important. your attorney has an escrow account let him handle the funds and execute the quitclaim after funds have cleared

If you have found a truly great deal due to your differentiated knowledge of the neighborhood/local RE market (i.e. having a reasonably good ARV estimate), or expertise in rehab, or some other differentiator that will give certainty of execution to the transaction, then it's worth putting your key terms/deal structure down on paper and focus on getting an anchor investor (debt or equity) so you can lock up the deal first.