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Id say your HOA is a keeper since you are investing your time in finding these things out for your contractor. PS, you may have a gem of a company too if he is really going so far and above for you.
Regarding your contract, id leave it open ended. I dont work on a specified time period contract. Every proposal I put out specifies that our relationship is perpetual and may be terminated at any time with a 30 day written notice (my commercials require "just cause"). I love it this way as I know that as long as I keep up my end of the contract that Im not going to be replaced any time soon. Besides, why would you want a fixed length contract? What lure does that have for you?
As was suggested above, if residents want additional services, they certainly need to pay accordingly.
What custom work are you talking about on a different day? Generally, I schedule all maintenance for a property on their given weekly day so that travel time is kept to an absolute minimum. There are exceptions but the further the site is from the shop, the more closely I folow my scheduling guidline.
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