Regarding insurance, I set the deductible at the highest the carrier allows – in my case $5k.

There is nothing quite like having a beachfront condo that generates income and allows you as the owner to use it as well.

should pet be allowed for rental? 

It doesn't allow me to enter the purchase price manually but I cannot put it in manually.

I could recommend plenty of people and place in or around you area, but I'm not allowed to do that in the forum.

http://hcidla.lacity.org/system/files_force/documents/Allowable%20Rent%20Increases_English.pdf?

What if I LEASE a home with the option to buy, does that allow me to bring in a tenant who i can then give the option to rent-to-own, even if i'm not the Owner??

Just make sure zoning allows for it.

Are there exceptions where a family member would be allowed to buy it?

Not sure what line of work you're in, or what level you're at, but it is pretty common these days for companies to be paying for relocation and/or a short-term housing allowance for new employees who have to move.