These properties cash flow using a $300/unit per month cap expense and 5% vacancy (our vacancy rate is less than this) and 5% maintenance expense.

As for Northern Michigan, the Traverse City area has become expensive and tourist-heavy. 

If the seller or tenants refuse to do this, then you can ask the seller to put 45 days of PITI + expenses in escrow with the remaining balance refundable back to the seller if the tenants move out earlier than 45 days (this however, does not guarantee that the tenants will move out within 45 days but it does put pressure on the now seller/landlord to push for option 1 - having the tenants sign something). 

Assuming 15k in repairs and you can refinance for 60K, then your break even rent amount (after expenses) comes close to $800.

These expenses can add up quickly and close in on your margin.  

With in 5-7 years I would like to be able to financially stable, that is to say that at this point I can cover all living expenses as well as be able to be able to purchase a car, or new appliances, or cover medical bills, all without having to worry about if I'll enough money to eat that week. 

Do you plan on using some sort of accounting software to keep track of income and expenses?

Insurance is a pass through expense to us (part of our monthly lease payment) so if we screw around filing claims and our rates go up that passes to us to. 

I've done a few flips in the past but the contractors were quite expensive and on the slower side for completing the work.

I average around $200/unit/month for regular operating expenses (many of which might not show up in first few months of ownership) and use around $50/unit/month for CapEx.