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. 

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

@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.

This can be a smoother, more amicable way to regain possession of the unit.Lastly, tapping into local landlord associations can be incredibly helpful.

A great place to find local networking groups is in the Events and Meet ups section of the forum.

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?)

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

If you have any doubts on the numbers, I would connect with a local expert like @Josh Green. 

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

)  - 60K in cash for downpayment +more for renovations- Strong local connections with contractors of all trades - Ability to get building materials at cost through family/business connections- Have a strong eye for style and design (Tends to lean on the high end of things as that is my business)  - 750+ Credit.