Only requiring first months and security right now.  

Keep an eye out for indicators of population increase or steady housing demand.The BRRRR approach may be appropriate for older properties, particularly if they require renovations.

If you were to purchase a property that does not require a lot of rehab, then you would be able to start renting within a couple of weeks.

No issues with property but state is requiring abatement.

This is a portfolio loan offered by local credit unions where you can buy up to 5 pure investment properties with as little as 5% down if you qualify, which you do have to qualify still with DTI, credit, reserve requirements, etc.  

I also don't know if changing the insurance policy would also require me to loose the homestead exemption and DV discount on the property taxes. 

Which entity do you require? 

If you were required to leave some sort of explanation for giving anyone a less than perfect rating, you'd probably either be justified (or felt justified), or if it wasn't something you wanted to spend time explaining you'd just give the 5. 

Make a note of any obvious maintenance or updates that are required.

Do lenders consider this a multi family and require commercial financing or is it considered a single family?