I make sure that the property has the ability to cover itself via rent in case of a market downturn during rehab.

., but I honestly have no idea how to determine major rehab cost or what detailed things to look for, in terms of structural damage, lead pipes, updating electrical, etc., when assessing a property.Any advice of this or do I just higher a contractor to walk the property with me and ask for their price evaluation?

While fees would be paid by the tenants, I'm concerned that this is basis for a reduced term rental permit and impact my ability to renew permits. 

Set your budget based on cash on hand or ability to raise and what you may qualify for with a mortgage.  2.

I am currently having conversations with a lender that will work with me on Home improvement loans giving me some options on improving distressed properties, but I will need to ask if they have ability to do wraps.

Even if you go bigger, they will still be looking at you and your ability to pay the mortgage, you will just be on the commercial side of the bank. 

I'm trying to determine whether the new rules regarding tenants will impact my ability to not renew month-to-month leases. 

I'm trying to determine what creative ways of financing I should look at here.

There are some financials you can only get from the current owner/agent - like T12, expenses, etc...But for rents, I would do your own research or contact your own PM company to determine what market rents are for the property.

As aforementioned, Rob has the knowledge, communication ability, and care to guide you throughout your investment process.