I think the insurance needs will depend on the overall strategy you are going to put into play and will change as the strategy progresses.

Waiting for the tenant to move in is the best bet

I bet my freezer has about $30 of food at any one time.

You have aggressively dropped down your student debt, I say continue the progress and pay it off for you can potentially buy a bigger home (4 fam) owner occupied once you are done.Or if you are comfortable with debt you can make a bigger return investing and that can help you pay down your debt. if you are I will get a owner occupied 2-4 family with a seller concession (depending how competitive your area is) for you won't have a high closing cost.

Make sure your numbers are accurate as during the rehab it can hurt you and become a big lost if you don't have the right numbers. your best bet is to partner up with some experience as the first deal can make or break you.

As you can see I'm really really focused on my future, I'm just at a standstill in life selling cars everyday and I feel as if I'm not progressing.

likely wont be allowed to  re use  appraisal ...your best bet to have a chance doing this will be to  work with same lender that just completed the  refinance …...in general  appraisals are  valid for 120 days

You should be rockin' the passive income.I never recommend building because, when the economy changed overnight in 2008, builders were the first to go and have still not come back in force.I never buy land - it's betting on the future.

The inherited tenant class, building condition, the financials and associated record keeping, bet you can't even find all the leases!

And he misses out on all the benefits of it being owner occupied, like tax exemption from capital gains because he doesnt actually own the property.I bet he isnt properly insured on the property either, because if he insured the property in the llcs namr, the lender would have been notified of the change in coverage.