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.

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.

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

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.

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

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

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

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.

The house rents for $1200 month currently and will be able to get $1600 if renovated (finish basement bathroom, new flooring and fixtures, mainly cosmetic).