We will always require at minimum 10% of a down payment for a purchase.

It sounds like you've done a lot of the preparation work required to hit the ground running. 

In the last 18 months various states have instituted new rules, regulations or laws related to (1) need for licensure to wholesale (2) restrictions on marketing of a property in which you do not have ownership and (3) disclosure requirements when dealing with a homeowner that makes it clear to the homeowner that the contact signed with the wholesaler is not a definitive “sales” contract, therefore making it less likely home owners will sign4.

Just to clarify, when I say timeline dates I don't mean just "project to be completed by (Date)"That's required by FHA/Lender, but in my 20 years of construction experience not nearly what you need haha. 

In Illinois for commercial property, property disclosures are not required. 

I think the companies are gonna start to crackdown on this pretty soon, all of the vendors require you to certify that you're not using the platform for cold calling.2) It works best for inbound leads, inbound calls and calling old leads to rekindle them.

If you have equity and decent credit, a conventional Fannie Mae HomeStyle (or the Freddie Mac version) would likely be the better option instead of an FHA 203k loan (which will require a 3rd party HUD consultant to oversee the deal in addition to having the contractor involved). 

Yes, sewer clean outs are required on new construction, but on a 1947 rehab house that didn’t have existing clean outs, is it really possible that I can be required to install them?

Using a HELOC for the down payment on the second home might be an option, but lenders may require you to wait a few months post-closing on the multi-family before approving new loans.The BRRRR-style approach could work if you can renovate and refinance quickly, but make sure the timeline aligns with your lender’s requirements.

I work with several who go to 600 or don't require a FICO for commercial at all.