For instance, Speedway, Beech Grove and Lawrence have additional rules in place.

So why work, why stress herself out, take on student debt, hours away from family doing that 9-5 all to achieve about $80kyr.

Give her 30 days notice now, keep her security deposit, and send her a additional bill for damages to the unit in lieu of taking her to court for the damages.  

I would appreciate any insights and additional things I may be missing.

A clean, neutral-looking curb gives prospective homebuyers a chance to visualize their own additions/upgrades.

To defer all of your gain, you'll want to trade up in value, replace all the debt (meaning new properties have at least $350,700 of debt), and not take any cash from the exchange (this is boot which = taxable gain).As for replacement property, it just has to be real property - meaning it can be commercial, STR, land, etc!

Am I getting greedy to ask for an additional seller credit at closing to help offset some of repairs needed?

Cash-flow is for "keeping the lights on" as in covering operational expenses to defend against any need for additional capital investment. 

These are professionals with additional training and a stricter code of ethics.

Additionally, I'm still not convinced that you are not associated with this new management company.