- Is form 1099-NEC filed through a software?

I have an applicant who makes good money and has decent credit.

Any insight, software recommendations, or recs on where to find a great VA would be greatly appreciated. 

You will need some type of accounting software to do this as you will need to input all funds you collect on behalf of an owner and disburse to owner or to venrods/government on owner's behalf. 

I'm pretty familiar with lead list builders such as Apollo, Clay, etc for enrichment, and pretty familiar with CRMs in general, so I think it should be an easy(ish) time getting a hang of the softwares!

It also integrates with most of the software you use to manage your business. 

The reason QuickBooks seems so intimadating, or any software program for that matter, is because we are using a computer to enter in our income and expenses instead of a piece of paper and a pen. 

You're not just losing time; you're likely missing Partial Asset Dispositions, like writing off the remaining 'book value' of that old water heater when you replaced it.Most of my clients at your scale move to a 'Class-based' system in QuickBooks or specialized REI software.

If it makes sense for you situation, definitely look into property management or maintenance software like Buildium, AppFolio, or TenantCloud. 

You aren't likely to have that many simultaneous applications for a property where you need something like this.