Assuming you "converted" the property to rental 4-5 years ago and you filed for rental applications/permits and have been filing 1040's for that property then you should be good from an age perspective. 

An experienced investor or vacation rental real estate professional familiar with local application processes and 'loop holes' can simplify the geographical areas of priority. 

I have a few questions about tenant screening.1) Do we screen all the applications simultaneously or screen one application after another based on first come, first served?

Only one couple has actually submitted an application.Although I need to verify some of their application details, it appears like they meet all my requirements.

Innago does everything that we need it to: communicate with tenants, listings, applications, leases, maintenance requests, invoicing, and rent collection...

Assets identified in this study include:Concrete paving and paversFencingEquipment padsConcrete sidewalksLandscapingThis engineering-based cost segregation study included the following methodology:Physical Inspection through a site visitDocumentation review including architectural plans, accounting records and construction documentsA cost analysis which utilizes engineering principles in order to allocate costs to their applicable asset classificationsCalculation of the depreciation schedule using MACRSAs a reminder, bonus depreciation started to phase out in 2023.

If you don't currently have a screening process I would suggest you create one immediately and include it in your application going forward.

However, from discussions with banks on about similar topics, I would say yes it is possible.My understanding is that you both would have to use the property as your primary residence, and you both would have to apply together on the loan application.  

Saying that vouchers are accepted in the ad brings plenty of section 8 applicants.

HOWEVER, a lender might look at your past history and not approve your application because they know even if you meet your obligation they are really underwriting an investment property.