If it's a family style single family home or multifamily unit, unfurnished, in non-core areas, the timing doesn't really matter as most likely your tenants a re locals who can relocate at any time regardless of the season. 

I was just curious if any other local investors in the area had a different take or feedback. 

It's got a village like feel with locally owned shops and eateries.

Send him a letter, emphasize that you are personally yourself the end-buyer, include proof of funds, include something attesting to you being financeable (unless your proof of funds is for the full cash purchase price).If he owns 20 local businesses, good chance he's in at least one chamber of commerce, and if he's not, he 100% knows people that are, who will spill the beans and offer to do an intro if you mention you're interested in buying a gas station over a beer or a meal (there's probably like 3 people in that city that fit this description, why not get introduced to all 3?)

Best bet would be to go to your local REIA and ask around. 

Call local handy man type contractors.

@Yusuke Koike if damage was that extensive where the unit is not habitable, check your state/local landlord tenant laws as some just require you let them out of lease, return deposit and refund rent for any time they’ve paid that they can’t live there.

The hard money lenders we deal with mainly focus on local rehabbers with history. 

Consider building a network of local contractors and service providers who can assist with property maintenance.

You'll see some familiar names thrown around a lot: Stessa, Apartments.com, RentRedi, TenantCloud, Innago, RentManager, Avail, Rentec Direct, Doorloop, etc.I think you should search for each app online and see what they offer, how much they charge, etc.