Anyone have alternatives they like?

You would never be allowed to choose a specific appraiser. 

Any specific tools to document the process or log the times?

You should be able to go to the cook county county website and look up the three pins and the related address.If there is an address where your name does not show up as the owner, I would then do the following1) Contact your mortgage company to clear up the confusion so they don't increase your monthly escrow amount and they don't incorrectly make the payment again in the future.2) Have a conversation with them to see what the resolution would be.They may offer a refund for their mistake.3) The alternative would be to have a conversation with cook county to see what recourse you have thereif the above don't work, you may need to consult with an attorney.

Make it a habit to create excellent content every day by allocating specific time for it.

If not, and I have to actually get a real estate license first, how do I find a sponsoring broker specifically interested in this arrangement?

So keep that in mind when you compare alternatives. 

But I think in such low end deals the fixed fees are kind of deal killers, hence was thinking of alternatives.

Specifically as a vacation rental.

Definitely check with your insurance company because I know this was one breed specifically mentioned by mine when I checked once I just started accepting pets.