Having someone on your side that has a current pulse of the market is priceless.As far as flipping is concerned, since you are remote, it'd be more ideal for you to be a money partner and not involved.  

 I found I deal that could be very profitable for me, but it's so hard to pull the trigger on something that isn't pretty,  only depreciates, and might be more work than I expect.  

Unit 1, 3 beds 1 ba, laundry room on floorUnit 2, 2 beds 1.5 ba, laundry room on floor(Unit G 2-3 beds maybe 1.5 ba ideally w/ laundry room.)Enclosed porch offers additional space for storage x 2.

Also while I'm on the subject, a lot of my nixies read "not deliverable as addressed" and I'm taking them verbatim off the local tax assessor website, so does that most likely mean there isn't a person by or close to the name registered with the post office matching who you've addressed your mail to? 

Line of credit... this would be ideal but we're not sure whether we can close on our LOC in time so we're taking it off the table (for now)3.

In my opinion I would list both LLC1 and LLC2 as named insureds on the policy, but you are more correct than the agent that LLC2 is the owning entity and they should the the first named insured, if only one can be applied, try a different underwriter.Now what makes this complicated is Florida is tough to place, but you are correct in wanting the named insured's to match up.  

If I had close to 30% of that to put down I wouldn't mind, just so I can stay in the area, as that would be ideal for me.

@Michael RichardsonIn section 1 of your initial question, you mentioned structuring a finance plan that matched your current mortgage with a balloon payment.  

As an investor I'm often in rougher parts of town at less than ideal times.

This will help vet those contractors looking to take advantage of folks, in particular since you’re investing from afarFocus on punctuality and communication – did they show up on time, did they return your call/email in a timely fashion, do they keep a well maintained vehicle, do they communicate in a professional mannerVerify IDOnline search of their name and companyReferences with phone numbers, and previous work – call the references, find out the type of work done, does the type of work they’ve done match with what you’re looking forGet a detailed, written scope of work (SOW) along with a detailed, itemized contract – define the payment scheduleHow will the payments be structured –are they asking for money upfront (potential red flag)Hire a licensed, insured contractor that is in good standing with the Better Business Bureau, and the local consumer protection agency; check the license number, insurance policy, and bond.