My three year goal is to provide greater help financially for my husband with our expenses.

We just had an conference call on this and a wrote a forum post yesterday about this exact circumstance and loan product..check in with @Joseph Chiofalo

We are using a hard money loan at 9.9%. 

That will help us provide you with better answers. 

An additional benefit of a detailed engineering-based Cost Segregation Study is that it can increase potential insurance premium savings as well as provides support for the property tax appeals process.

If you go the LLC route, PM me up because my wife broker's commercial deals which are much cheaper than DSCR loans and you can't get a Conventional loan in the name of an LLC.

Brokers (versed in these development deals to help you negotiate the right contract terms), Lenders willing to fund a construction and permanent loan, architects & engineers vs in land development to help site plan the project, contractors to price the project to help dial in your UW. 

I'm definitely new and I don't have all the logistics planned out this is just the vision now I'm trying to backwards engineer and figure out my steps I thought my first step would be to househack a 4-Plex on an FHA loan and then graduate to six or 12 units and then move on to bigger properties most likely outside of Chicago to your point. right now I am very confused this is the second time someone has said that four unit is not like a six or 12 but I'm not really sure in what ways is it the underwriting is it the management is it literally every aspect of it.

Homeowners might have different needs that a single package can't fully meet, and getting everyone to agree on one provider could be a challenge.

Bank said the land was only worth 200k and that’s all they would loan.