Your starting location makes a huge difference in the amount of overnight stops.
The high number of stops in the hill country are easy day trips for you, for me, requires multi night stops. I never got near Dallas, since all those are also overnight (unless I want to have a 14+ hour day).
Well, I ride an FJR and a Wing, and don't think anything of long days in the saddle. You're only two hours south of me, and much closer to some of the coast stops both years, and South Padre last year, which was one of my three overnight stops. As far as Dallas, depending on what roads you take, you're under 4 hours away, which is only about one hour more than me.
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