Hi Jordan,
I have read your request about custom fields that you want to create. I think you can create almost custom fields that you need. Beside it, i have 3 problems you need to know
1. Custom fields is one feature of OS Property, it allows administrator to create new extra fields to store the property's information. It's not "Form" function like Chronoform extension or something like that, so between the extra fields, we don't have any relation. So it's impossible to implement the feature : after field 1 is clicked -> field 2 is appeared
2. The extra fields are use to store and show data. It can't be used to calculate the amount and processing payment gateway
3. The extra fields are be-ing shown at "Add property form" and "advanced search form", and OS Property doesn't have option to show extra fields in specific areas as your request.
In general, the best way is you hack into core of OS Property to add the fixed fields instead of using custom extra fields.
Thanks
Dam