I’d love to house hack and start with a duplex or larger, but I’m just finding is hard to shop around in our market.

To avoid this, it’s best to work with a broker who can shop around and present you with options from multiple lenders without multiple credit pulls.

As someone who deals and talks to real Private Lenders (small shops run by a guy who lends his own capital and doesn't use big box), they have a hard and fast business model that produces the rate of return they need to remain profitable and curb the risk on their cash.So the best product for a budding fix and flip investor is the bridge loan which includes acquisition money and construction money. 

I just keep a running shopping cart throughout the day/week.

The typical clients that seek out cost segregation studies include:Real estate companies that buy and sell multiple properties each year.Individuals with a portfolio containing investment properties including apartment buildings, multi-family homes and even single residences.Franchise owners with properties that are similar to one another such as assisted living facilities, storage facilities and golf courses.Business owners of hotels, food facilities, shopping centers, restaurants or manufacturing plants.It depends on the type of property, but generally 15-45% of the building’s costs can be classified into assets with a shorter life.

The very basics would be getting your furniture and shopping list together, keyless entry like Schlage (with backup lockbox with physical key very close as well), looking into insurance, local taxes for STRs, and moreAlot of ways to save time and make it easier to self manage with a property management software like Hospitable and data research like AirDNA.

I have already shopped insurance, and the sellers are providing $5k towards prepaids/closing costs. 

You’ve got to follow the rules closely, and that means working with a qualified intermediary (QI) who’ll hold your funds in escrow while you shop around.

Depending on property titling one partner can get the conventional financing and the other can make a gift or use their assets for the remainder.  

I did not read the rules around security deposits. you may be allowed to use those funds and still file a small claims action for any remainder, but I can't imagine that it would be worth it if you have at least one month's rent in security deposit.