I strongly recommend getting involved with your local REI meetup groups so you can work out your pitch with help from other landlords.I hope this doesn't come off the wrong way without tone or facial expressions behind it. 

It’s great to hear that you’re already active in the Southern Maine market.

I don’t have a specific recommendation off the top of my head, but for HOA/condo insurance, it’s usually best to start with a broker who specializes in multifamily or association policies.

If worse comes to worse and I need to get a judgement against the tenant and co-signer(s) can I force them to pay?!?

The amount of capital required depends on the city's appreciation rate.

Also, if you buy using a hard money lender or cash, Zach Starnes can do re-fi's off the appraised value shorter than the typical 6mos and then you might not need any money down if you buy at the right price.

I spent 2.5 years getting all the utilities to the property.

Sounds like I can safely write them off only after I purchase the rental and start the renovations to ultimately rent it out.

It takes 2-3 years to get it off the ground and adding investing in the mix would be too much.

If the market is tough, I reduce the rent rate over the full 12-month term.