I am working on getting the exterior painted and one of the units will need a full remodel.

Sounds like you need to have a relationship with a couple of good contractors, 40k for vinyl siding sounds high, what was the material cost.  

All the guest rooms have separate exterior entrances so we put keycode locks on those and guests get the code via text a day or two before they arrive. 

Did you put in the carpet when all the properties in the comps you pulled are selling with luxury vinyl..

New interior and exterior paint.

The finishes include ceramic tile, modern light fixtures and luxury vinyl plank flooring.

+1 for Schlage Encode and a name brand camera - we do front and exterior sides and leave backyards private.

There is intact and poor condition, poor condition needs to be either wet-scraped (removed) or encapsulated (think vinyl, etc.). 

Property taxes creep up, exterior repairs , and a brand new HVAC last year wiped out $11k of reserves.

@John BarryFirst and foremost, Section 8 is a protected class in Massachusetts, so you can not discriminate against any tenant that has it.As for the steps.1. list and show the unit as usual.2. validate all tenants the same way.3. if you go with a section 8 tenant, then they will have paperwork for you to complete/submit.4. section 8 will send out an inspector to check the unit, all common areas, the exterior and the basement (does not matter if they have access to it or not).5.