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 think you'll have an easier time getting started. 

Work backwards from your $300,000 annual target to monthly say $25,000 per month.  

We use a third party servicer to do all of this - much easier and when starting just tracked payments in wuickbooks as servicer tracked everything else 

A smaller paid off portfolio seemed a lot easier to manage so that is the path I was on.. but I've come to the realization if I ever want to accumulate serious wealth I will have to use leverage and scale big. 

So, if deadline not met, we will send our people to handle.4) Vacant properties are easier to deal with, but we still require:- Owner must sign a Hold Harmless to indemnify us against any potential lawsuits relating to the work their contractor is doing and add us to contractor's insurance.--- Another lawsuit from a prospective tenant that slipped during a showing and when they grabbed the handrail, installed by owner's contractor, it collapsed and person injured.- Since we're not really in full control of the property, the Hold Harmless also indemnifies us against anything that goes missing at the property and squatters.We get asked/told to do all kinds of crazy stuff by owners, who either don't care what happens to us or haven't really thought everything through.Hope this addresses your question.

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.

For example "Just get 3 estimates from general contractors.." is a lot easier written than done!!

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

What financial targets do you have?