If you have fewer than 20 units, I think spreadsheets are sufficient for tracking everything.

This gives you both a choice of which is a more qualified tenant AND the opportunity to ask for highest and best (yes, you can treat multiple applications like multiple offers).

When a applicant does not provide sufficient information there is no point in you doing the leg work for them, they are hiding something.

Mason, you're in for a discovery...you really do not have any choice but to include utilities in the rent unless you're planning on installing sub-meters. 

So most of your choices will be Single Family homes.  

The poor guy is getting screwed, but it's his choice.

I have replaced dozes of sewer lines in Cleveland, just replace it, no other choice, 12k seems about right

It may be a “chocolate or vanilla” kind of choice.

I see a lot of assumptions / misconceptions about my personal situation in the responses so I’ll try to clarify a few — obviously language isn’t perfect, certainly my choice of wording isn’t, and I also didn’t want to write a full dissertation about my personal background [nor make you read it] before starting.

Good day2 choices here:1.