Generally speaking advantageous tax treatment follows.Assuming active participation and AGI is below phase-out, expensed items will reduce taxable income, which seems like mainly W-2 income.Consult with your CPA/EA.

Cash flow is not important at all; my main interest is going free & clear on this property.  

@Darryl JacksonHow much you need can depend on many factors , the purchase price of the home , the rehab costs etc.Also if you are going to pay all cash or leverage ( hard money or private money loans etc ) If you don’t own your own home I’d suggest doing a live in flip or house hack as you can take advantage of low money down loans like an FHA loan for 3.5%Many people have used this as a way to start out and gain equity that they then use for other deals .It’s possible to do deals without your own money if you do a joint venture type deal but could be hard to find someone to partner without experience, might have to give up more than half the profit but still better than no deal .

I am in the process of purchasing a triplex in central Maine and was wondering about insurance company options out there.

I was very excited.The only problem that we found was that during the sewer inspection, the guy said he ran into some problem with the main line where the camera got stuck but he didn't know exactly what the issue is. 

The main entrance has an office, multi purpose room, bathroom and coin-op laundry room.

Unless you plan on doing all the work yourself, you should factor in termite inspection/prevention, possible tree removal/trimming, clearing gutters to prevent leaks, sending contractors to fix things that break, painting unit after each tenant, changing locks after each tenant, cleaning, appliance maintenance etc. 

My main goal is achieving financial freedom as quick as possible.

Finding the right contractors to renovate at a reasonable price and time frame is another very important factor, as well.

Maybe on the high end but there are other factors to consider.