I agree with @Mike Dymski, savings and budget (especially for newer investors) is vital to an investor's growth.

Also, once lease is signed can this (so far very high maintenance) tenant demand modification on this single family home which is our only rental?

You will need to start from the forum and resource areas..then the podcasts..loads of loads of vital materials to digest!.. 

I have a background in mortgages, loan modifications and short sales. 

None of this was speaking to the potential disposition of forbearance or modification.

I am doing option 1 for one place and option 3 for another place as modifications in that place might lead to code complicance complications with the grandfathered location of some stuff.

I agree with @Bob Ebaugh and @Tammy Vitale - $1k over asking is not that much, depending on how the property was priced.

When you do the title search, some properties will have lots of recordings - things like deed transfers back and forth, multiple mortgages in place at the same time, subordinations, mortgage modifications - all of these sorts of things add complexity.

I also have extensive experience negotiating short sales, OREO sales, DIL, modifications, and mediations.

Where you begin is understanding the "in the box" requirements, then while remaining compliant with those "in the box laws and rules" you adopt modifications or changes (keeping with legal requirements) to come to solutions that meet the needs of the parties concerned.