Do I run into issues if I / myself can't get the dwelling ready for the listed date?

From Section 121(b)(5): (emphasis mine)(C)Period of nonqualified useFor purposes of this paragraph— i period of nonqualified use” means any period (other than the portion of any period preceding January 1, 2009) during which the property is not used as the principal residence of the taxpayer or the taxpayer’s spouse or former spouse.ii period of nonqualified use” does not include—portion of the 5-year period described in subsection (a) which is after the last date that such property is used as the principal residence of the taxpayer or the taxpayer’s spouseThe law does not mention anything about how the property was FIRST used.

You'd be far better off to see if your county has public access to mortgages in arrears notices notices online somewhere, and pursue the preforclosure route, as best as I can tell.

In Florida, if they only pay half, and we accept payment, we draw up a stipulation which states that the remaining rent will be paid on xxxx date, if not paid on that date, the eviction continues as if it never stopped.

Establish move-in date.8.

Aside from making deposits, most of my expenses are auto pay and made through my online banking.  

But you don't need Legal Zoom to create the LLC, you can do that online mass.gov for just the filing fee. 

According to the mass Landlord / Tenant laws: "On the anniversary date of the tenancy, you must send the tenant a statement of the interest owed with a check for the interest, or you must notify the tenant that s/he may deduct it from the next rental payment"Sorry if I'm talking in circles, I'm just trying to understand if there's anyway I can remove myself from this process while at the same time making sure the tenant gets their interest in the form of a check every year...

If the move out date comes and goes then take the necessary actions.

You could set a goal to save a certain amount of money by date xyz, call a certain number of lenders, connect with certain number of brokers/agents, know x-amount of investors,  build your network slowly but surely.