Bear in mind that I'm not interested in flipping or extensive rehabs, so I'm in a particular niche. 

And if they do expire, what would I need to do to get an extension?

The state, utility companies, contractors, etc. 

My advice would to find some more extensive projects and get those rolling through the winter and have them ready to go in January/February/March. 

2 - Is it common for the RE agent representing the buyer/seller to be anxious and annoying during this process when continuing to request extensions?

Do CODE VIOLATION SEARCH.9Calculate MAX Bid PriceOnce the properties are filtered with the above criteria, set the max bid price between 60% and 75% of Fair Market Value or ARV10Bid StrategyDetermine the low starting and maximum bidding amount, to be agreed by GENERAL PARTNERS11BiddingEnsure 5% of max bid price is in County bidding bank account 3 days prior to bidding12Property Win BidEnsure funds are wired to County bank within 24 hours of WIN13Send File to Lawyer/Title SearchIf property is still occupied, have Legal file a “Writ of Possession” to get former owner removed, Perform Extensive Title Review, Negotiate any existing Liens14Receive TitleReceipt of Certificate of Purchase, Certificate of Title to occur within 3-4 weeks from date of winning Bid, continue follow up with County until received

I will be utilizing this means (as well as others) to implement the "retirement" phase of my life. 

My tenant just moved in and has not switched utilities over in her name yet.

I will sell it to him for $1He agreed to pay $12,500 in 12 months to cover the money I have invested in it ( Down payment)  and some 3,000 Profit For MeHe also agreed to pay all the utilities, and all repairs, damages that the house may need, now and later.  

Long time tenants are on month to month leases and utilities is currently included with the rent.