Beg family and friends to fund it for you.They "might" do it if they see you've learned a lot and your business plan sounds very solid.How do I know this "might" work?

Would you rather set it and forget it and not need to refi again or rather take advantage of low/no closing costs on this loan and plan to be more aggressive on your rate at the time of your refi?

Just be sure they have a strong plan in place to market your properties quickly and that you thoroughly vet their tenant screening process to ensure minimal vacancy and high-quality tenants.Ultimately, finding the right PM should make your life easier, not harder.

I've done and been a part of many Chicago zoning changes...they take a very long time and a lot of upfront money...unless you are planning to add multiple units and do a full renovation, the ROI is probably not there.

With the exception of building a trailer on the property (these are hard to finance), this sounds like a good plan AND if you are using it for your business AND your business pays more than 50% of the rent (if you have more than 1 tenant), then this is a more financeable property in the eyes of banks and credit unions as it would be consider a commercial "owner-occupied" property. 

I am currently 36 years old and planning to start my real estate investing journey this year.

I have a similar project in Buffalo NY, however, I had to change plans when I got further into regulations.  

NOTE: we charge extra for this.4) What about a floor plan, so prospective tenants can get an idea where their furniture may fit?

Listen to podcasts, read books, and if you plan to invest in the Netherlands find some resources that speak to that market specifically.

 Hi Roger, yes, the plan is to house hack.