I really appreciate your thorough explanation, and love everyone's opinion. 

Other downsides to going this route: the process to get the unit approved can be long and tedious; the apartment has to pass section 8 inspection - they are thorough, and go by the book.

We are focused on Connecticut properties.So far we have looked thoroughly into List Source and Datatree but not sold on either company.Please share what sites/companies you have had success with. 

I'm a little surprised you're reacting to Paul above who said the truth. when you ask advice, it's better to listen and not assume you know more than they do using something like vacasa or TurnKey or evolve is a gigantic waste of money. the keys are to be on the four major booking sites, use Dynamic pricing also called yield management, read this form thoroughly for the last few months to get background knowledge, automated as much as reasonably possible, learn to self manage even from a distance, and get a good property management system such as ownerreservations or guesty for channel management or something similar. 

Lenders can be annoyingly thorough about having a second home with a mortgage.

I had an amazing agent (Patricia O’Neil with Keller Williams) who was my boots on the ground and I paid for a thorough inspection.

Most states do not allow the landlord to show up to the property without proper notice, so your tenants will need to be notified before the visit.During the visit, you can thoroughly check your property and ask your tenants about any issues they may be experiencing.All the best!

Wait until it is actually vacant, and you have had the opportunity to thoroughly assess what needs repair or updating.

Hire a professional inspector: Hiring a professional inspector can give you a more thorough understanding of the condition of your property.

Tenant lives in a fairly new SFH that has been thoroughly cleaned and everything broken repaired prior to tenant moving in.What is your strategy to politely let the tenant know that this is not a luxury hotel or all inclusive resort ?