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. 

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. 

It'll be easier to manage and you could have less frequent turnover. 

Some operators close upon tenant moving in .. some when they get CO  myself I always try to get them to close before tenant makes the transaction much easier on the seller not having to interrupt the tenant and doing punch list much easier then put the tenant in.. in my mind if you are going to have an issue losing one month of rent because of this your being unrealistic for a long term hold your going to have vacancy at some point so why not the first month. 

Being clear about what you want to do from the start not only helps you stay on track, but it also makes it easier to spot problems or delays before they happen.I totally agree that talking to people is important.

I've recently ended my service with them and things are so much easier and less expensive.

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.

I would just excavate a few 2'x2'x2' (or larger if possible) spot footings, w rebar and Simpson hardware,under the house (you will want to take up the floor to make this easier to do).

Here’s our OPINION for the Metro Detroit market (use as a template for your target area!)

Sometimes, landlords can find student renters for locations that are further away from the school by targeting niche's like graduate students (who are less inclined to be near the bars and noise).