The articles I’m reading have me confused on whether or not I’m supposed to step in and catch her water bill up (three months worth so 180ish plus late fees).

You could tell them they can live in the nice unit at +50  for three months and if they like it will go up to market after that, (or some similar incentive) to get them out of the old unit so you can remodel. give them a "discount" on the nice unit for 1 year?

As a landlord I've used it three times and twice they were very helpful.The landlords have to give the 2 months' notice to the tenants and they should keep that as it outlines why they need to move. 

My three year picture includes approximately 5 employees to support my revenue goal.

Both of you are on title (well all three). 

My tenant died and has three months of prepaid rent.

It took three weeks to hand-write all those letters, $550 in stamps, $120 in envelopes, and all of those inputs gained zero output. 

-I know of three meetups.

I've definitely learned three valuable lessons: 1) the importance of making sure the tenants change filters regularly (and understand the consequences if they don't); 2) the importance of talking directly with the vendor prior to any visits, and specifically re: discussing pricing and preauthorization / do not exceed limits, etc.; 3) and that I shouldn't waste my time and energy on worrying about an "issue" as small as this (that is to say, worrying and spending time after the fact, after the work has been done).

Personally, I keep rents just under market to minimize vacancy, but if your interest from qualified (important that you distinguish qualified applicants from random people responding with a click to your post) renters is more than three in the first week, your price is probably too low and you should just raise it and check if the applicants are okay with it.