Companies established after acquisition date

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I'd greatly appreciate some advice on outbound marketing and PPC advertising in the scenario where you have names that were acquired/registered before a company/site came into existence.

I've bought up some future tech domains, every now and again I like to keep an eye on the keywords. I've discovered about 5 of the names I registered are now fully fledged businesses in variants of the names I grabbed.

Example I own VR+keword and thevr+keyword and keyword+vr and other variants are developed sites. Is outbound marketing to these businesses considered a form of bad faith? Is it wiser to sit and wait in the hope they'll eventually reach out?

PPC Parking

Another situation cropped up that i'm not clued that's similar to above, but with PPC parking. I acquired the domain long before they launched or even owned their domain. I generally avoid PPC unless the domain is earning enough and there's no tm risks. This domain name is entirely generic and there's a host of businesses using the same or very similar variants of the keyword in this niche.

I own niche+keyword, a company has registered and developed i+niche+keyword, they are advertising on PPC and they have also filed for a tm.

The name earns enough to warrant parking with occasional $xx clicks. The company in question above recently approached me about the domain. Would it be risky to park if they opt not to acquire it? I took it off PPC parking one month before they contacted me to test if inbound leads increased.

I've decided to develop it in the event they don't acquire it, it'd be nice continue having the name pay off its acquisition cost while in the dev pipeline. Obviously I don't want to open myself up to any potential tm conflict and udrp trouble. I'm guessing it's safer at this point to avoid PPC parking?
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