Almost no established investors / flippers want to borrow a small amount of money from a brand new investor.  

This is the metric typically used on row homes or twins, detached structures usually add landscape or more siding and a higher likelihood of pitched & shingled roof.

You all would establish the term that the seller would finance.

I was planning to establish a single member LLC (my third) to represent this new venture.

This includes all structural drawings, exterior drawings, framing plan, mechanical plans, plumbing plans, electrical plans, gas line plans, roof layout plan.I tried to work with a couple of firms and the pricing for all these came all over the places.I also came across a company called flip16.com (September Development, LLC)  who said they can do all of the civil engineering and architectural drawings work at a fraction of the price compared to those civil engineering and architectural firms.

Illinois REIA was established in 2015.

That is until a roof or an hvac unit fails.

What would you say are the biggest advantages of developing a solid core-4 vs. a more established turnkey company that are a few clicks?

Many of these properties are undervalued and can provide great returns once you establish solid tenants.I'd be happy to guide you through your options, whether you're interested in house hacking or building an investment portfolio. 

Roof Replacement depreciation deduction.How to calculate Roof Replacement deduction.