@Michael Wyatt do you have recommendations on any specific software that can help me analyze properties 

I spoke with State Farm, but they require plumbing and electrical panel upgrades just to consider reviewing my application.

Applications were being lost, or the website wasn't permitting tenants to fill them out.

Depending on what softwares you use they can usually pay for the background check themselves.

And, Turbo tax Business software is $163.

I highly recommend investing in a property management software, such as Hospitable, for syncing your calendar, automating messaging, and scheduling cleans, as well as a dynamic pricing tool, such as PriceLabs, for optimizing your pricing based on market demand, local events, and seasonality. 

I'm looking for the cleanest & most visible way to access payment history, see amortization schedule, tax documents, etc- much like bank softwares provide. 

That affects your loan amount and then principal & interest payment.2) Estimate rents based on recent rental comps3) Account for all operating expenses such as property taxes, insurance, repairs & maintenance (landscaping, snow removal, cleaning etc), property management (if applicable), vacancy, utilities (what does the tenant pay vs what you would pay?)

We use the collection service through our PM software, but most of these folks become virtually uncollectable at a certain point. 

We currently don’t accept sections 8 applications.