For example you can build an ADU to rent out as an STR and stay in your main house, since this is still your primary residence it seems that would be an allowable use.

Personally, I would recommend purchasing the primary residence first, mainly because of how the DTI is calculated.Scenario 1: If you were to purchase the STR first, and then the primary residence, you will likely need to qualify with the full payments on both properties depending on your timeline.

Live in the basement and rent out the main floor.

I own a successful construction company that mainly focuses on kitchens, bathrooms and interior remodels and have been in business for over 4 years.

Mulifamily is already being built across from the Field house called the "Main". 

I think the main issue I see with this is the insurance carrier not accepting escrow payments.

If your main objective is cash flow, most of the times it makes more sense to self manage your portfolio.

To Service or Not to ServiceIn the world of distressed second mortgages, we use servicing companies for two main reasons.

Just posts that say get a lot of quotes because they can vary considerably.Need to replace a supply line from the main to the house.

Lastly, this loan would need to be heavily dependent on the actual property instead of my tax returns as I just quit my job a few months back to go full-time into Real Estate.Hey Wil,A lot of information to sift through, but honestly I think your toughest element is the 'at or around 8%' right now.