They may advise that you submit a claim to the Insurance company for the Association and make them state why the damage from the leak is not covered. 

So we have an online portal for contractors to submit bids and SoW.He said he will submit everything except the license number and never had a lender require it.

I'm seeing that a lot of the municipalities will allow homeowners to submit building permits, but will place limitations on residency requirements and property types (i.e., not allowed on townhomes or condos, must be primary residence for 1 year).

I think finding an investor friendly agent can help you spot hidden gems like that and submit offers on your behalf that fit your buy criteria.

Is there any reason I need to submit the deed to the county now or could I wait until much closer to when I plan to refi?

Recently submitting an appeal for my house, I was told that there is a rick that an appeal could lead to a higher assessment if it's found your is undervalued; typically uncommon in Cook County. https://taxbacknow.com/

Submit Deed of Trust - OR - Mortgage (since it's Oklahoma) along with Purchase Agreement?

@Jay LevyTo make things really easy and simple I just use Zillow and have potential renters submit an application thru there.

Next year submit a new increase. 

Update- After dealing with a couple different realtors and submitting offers.