Old and expired listing are from people who want to sell but didn't find anybody to buy at their price. 

No question you are 100% stuck with this lease until it expires.

The permit states it is a 3-family home but subject to: 1) The town building department having the right to enter the premise with 24 hours notice 1x a year to ensure the home is in compliance with the town's codes2) The special permit will expire after 7 years and a new permit has to obtained 3) The special permit may be revoked if the owner violates any of the town's codes Is this "Special Permit" worth the additional headaches of the yearly inspections and 7 year renewals? 

In theory, if you show the current lease showing that the lease will expire/renew on X date, and then a letter from the renter stating their intentions, this should be ok to have underwriting approval. 

I've targeted expired listings in the past with a very high response rate, but haven't had much luck converting.

Account Closed  Your offers should always include an expiration date, otherwise the seller could accept your offer at any time - and that could be a problem if you've moved on to another property.Also, the way you worded your post makes it sound like you had two active offers at the same time. 

However values can be disputed or if you just wait long enough they expire and then you get to try again.

Any increases will have to be timed with lease expirations/renewals.

Once the tenant on lease expires keep them on M2M until you are ready to move to that unit to renovate.

I thought I'd be trapped in that contract until it expired.