Thanks for the feedback.
As far as GC'ing goes, I can assure you I didn't take anything from a "webinar." I GC'ed a house when I was 24 years old, and have built and been in the trades since younger than that. GC'ing is not my current gig, but is certainly not foreign to me.
Points taken about the risk of owning two properties and spreading pretty thin, it makes me a bit nervous also. I think what reassures me is knowing the local market pretty well and betting that worst case scenario I end up with a paid for house, even if I cannot sell my current for top dollar.
That is assuming there is not a major market meltdown. The only downswing I have really lived through so far was 2008, so my mind always thinks catastrophically when I think about market ups and downs.
Trouble with selling now are the straight up logistics of doing it, getting on the market, finding trailer, making it livable, keeping SO happy throughout, finding a place for all our crap. All in the coldest, darkest, wettest season. Of course it is all doable, just hard to swallow as I sit in a cozy home by the wood stove and type.
But this is exactly the feedback I was hoping for. Sometimes you can really get tunnel vision toward a project or toward a goal and lose sight of things.
Being able to ask questions to an unbiased audience is really helpful.