beselfish, are you aware the SR-125 has been built thru this area since the OP? HOWEVER, it costs nearly $5 per use to travel its entire length (about 9.5 mi). Windingwalk is one of the furthest-out communities in Otay Ranch (abt 22 mi from dtn SD). If you lived there and wanted to skip the toll road, I have heard it takes 35+ minutes to crawl to I-805 during rush hour on Olympic Pkwy or Otay Lakes/Telegraph Cyn Rd (just to enter the fwy). Then you have the stop and go fwy traffic northbound until about 8:20 am. For this reason, it is NOT a convenient area for a northbound “worker bee” to live in.
The vast majority of the communities in Otay Ranch (esp Windingwalk) are built VERY tight and offer little privacy. In addition, some of them have two or more HOA encumbrances and ALL have MR, as you are aware.
IMO, you can get a LOT more “bang for the buck” buying an SFR in 91902, 91910, 91911 and 91914 (Rolling Hills Ranch only) while avoiding MR and minimal or zero HOA dues. In addition, you will likely get a lot between 6000 and 14,000 sf (up to 22,000 for a heavy “fixer”) for the same prices as the asking prices of new construction in the southeastern portion of Otay Ranch.