Bonus question: if you own each unit in a condo development, can you avoid the HOA?

That $15k+ was like a bonus for diving in early in COVID.

Until I see that category with a $0 beside it, I'm going to consider it as an expense.  

The short answer is that yes, certain categories of retail such as apparel, consumer electronics and department stores, which are vulnerable to eCommerce, have been hit harder than others.  

Rather, it should be looked at as a bonus!

I just use Quicken, set categories to match Schedule E, then use tags to designate which property.

Given the totality of what you posted, you probably need the "tip" income from your job to "count," which will indeed only be counted after it appears on a couple years of tax returns.The base salary component of your income can be counted right away provided you work full time, with the college transcripts potentially serving to satisfy 2 year work history requirement, but that tip/bonus/overtime/whatever component needs to be on a couple years of tax returns.

Enter your transactions like any other ledger but include a column for expense category.

They compensate this guys with a 50k/year package that includes free rent, salary, bonuses, etc.

If your rental is in an area where it is uncommon to provide laundry services, this will be seen as a bonus.