We are using a hard money loan at 9.9%. 

Conventional loans for primary residents are the only loans you will ever get that have the ability to put so little down so you should take advantage of it.

Roam buyers save up to 50% on monthly mortgage payments compared to those who buy a home with a traditional mortgage at current rates." is what the company keeps on pushing out from a PR front, but it just sounds suspicious to me.

The most pressing, and i cant seem to find a true answer from the the building department OR the utility companies is if I need to have separate meters (Electrical, gas, water) for my ADU and main home. 

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.

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.

Also, the insurance companies are fleeing Florida so I'm definitely not making as much as I would from selling while things are still good.Talk me off the cliff or push me over please.

You would probably have to partner with someone who has a track record, or at least a reputable GC, in order for a lender to consider you for a construction loan.

In that case, I refused to close on the loan.

To secure the construction loan for the duplex, I would use the entire property as collateral to meet the down payment requirements.Does this sound like a good strategy?