The advantage with CrowdStreet is that they vet (or at least claim to) thus living you really mostly with DD on each deal.On SFRs, I think this is where the real impact due to ability to leverage our own cash.  

If that is the case then Mom and Dad claim it as a Primary and you don't claim anything.If you are securing the debt on the property making loan payments and the such then it would fall into the realm of a second property.

Insurance company denied claim due to property being vacant for 60 days.

It's those maniacs that buy homes cash via quit claim deed off of craigslist that really get screwed.Make sure your property manager is a licensed real estate brokerage.Google Clayton Morris and/or Morris Invest for a cautionary tale of what not to do when buying turnkey real estateUnderstand you can not eliminate all risk, only mitigate it.

I'm going to go through the process and file a claim to see where this takes me, but would I be able to demand the HOA replace or repair my cabinets if insurance doesn't cover it? 

And as far as a future 1031 exchange - If my intention was to to roll these funds into another flip, and roll those funds into another one, my understanding is I would need to have the NEXT property to flip already claimed to do a 1031 exchange? 

You won't be able to claim the lost income from missed opportunity costs.Best strategy is to let the borrower sell the property.

I'd talk to a known local attorney then if you need legal docs and contracts, and get them custom tailored to whatever complex deal you are working on....  

I had reached out to a previous customer of mine that I did a kitchen and bathroom remodel for and asked him if he was interested in investing.

Oh, I have bought many properties in this situation.Here are my pointers/lessons learned:1) Make sure you understand the deposits and they are included in closing2) Make sure you understand your state laws on giving the tenant notices to move out3) Try your best to communicate with the tenant some will freak out when a new landlord is added.4) Get a copy ownership to the new tenant and make sure to get keys5) Inform new tenant by your state laws you need to do repairs and get pictures before damage is done that they claim was pre-existing....bs.6) Be nice but be strict when it comes to paying on time, they will test you.7) Hope for the best, and prepare for the worse.