I'm not too hung up on this, because the margins still appear very attractive (from what the agent speculated ARV). my hesitancy stems from a lack of experience and direct steps/plan of action to take on a property I like. 

Once you get past the initial learning curve and have some basic knowledge, it gets a lot easier though and at that point most knowledge gaps can be filled as they come up.

We will both keep our W2 employment for the near future just looking into getting an extra income or make our retirement easier.

I know her prediction doesn't state today, but for activity to jump in February and then again in May to June that doesn't appear to be in a common volume trend of a "normal" year if that exists anymore!

My expertise is property management & I could help you with how to choose the right property management company, but it appears you are planning on self-managing.

Instead I will tell you that it can be done and you just need to have a quick call to go over the basics and be able to answer several questions.If you wanted to buy an investment property that would be even easier and there are a few programs you could use for this as well.

Absolutely.If a landlord is listed as additional insured (rather than additional interest) they cannot make a claim against one another's liability policy for damages - it could completely jeopardize the coverage they think they're making it easier to get. 

.,) relative to all other applicants, but after showing them the property you have the distinct sense they'll be a difficult, high maintenance/game-the-system/treat-your-property-poorly tenant.Essentially: how do you stay on the right side of the law rejecting a tenant that appears to be the best applicant on paper, but to whom you don't want to rent based on unpleasant personal interactions or impressions that they would likely take poor care of your property?

I understand Vermont has slightly more stringent regulations to contend with but it would also be closer for us geographically and thus potentially easier to manage. 

I may consider more passive investments , but that appears hard to come by.