Welcome back bourne. Thank you so much for summing up the entire case - it's very helpful to see all the circumstances through fresh eyes.
My thoughts about Bob being picked up on the street are that it is unlikely for a couple of reasons; if you look on the map, Carnation Drive ends in a cul de sac, as do many of the streets around it. It just doesn't look like a good place for a potential abductor to drive up and down, without having to turn their vehicle around and draw attention to themselves by passing back the way they had just come. A street abduction seems like a really risky strategy too.
The other thing that bothers me about that scenario is that Bob was reported to have not taken his glasses with him (at least originally. That too, has been 'subject to change'.) His friend said he wore them everywhere.
You're welcome!
Having very limited (and also some inconsistent) information to go on -- basically from only the Disappeared episode, some legal documents, and my skimming of insightful posts from this forum -- it's challenging to conclude with any certainty what exactly happened to sweet Bob.
I can say that immediately upon finishing watching the episode for the second time was that I felt:
a) Bob was still depressed when he was on the wedding interview (and I recall the narrator of the episode stating that their wedding was EXACTLY a month to the day he disappeared -- so it's possible Bob disappeared on his own);
b) Bob made a list of repairs for Jeff (so it didn't appear Jeff was lying about doing home improvements on Monday for Fontelle's impending arrival on Wed);
c) Daughter Paula was likely NOT in on Bob's disappearance. It's hard to imagine someone that heartbroken about witnessing her dad's emotional breakdown during and after her mom's illness and subsequent death being involved in harming Bob. JMO based on years of clinical work...
Re: Bob's eyeglasses. That was not mentioned at all in the episode. But I do recall earlier reading that his glasses were not found at the home but that in later days his daughters then claimed he had several pairs. I'm inclined to believe that Bob had more than one pair, because if he's as meticulous a person as I believe he is, he likely owns at least two pairs of eyeglasses -- for the just-in-case situations whereby one pair is broken, etc. So I think he did have at least two pairs of eyeglasses.
What I'd like to know is whether LE ascertained how many pairs he had, and whether his daughters were aware when he would switch glasses...I know in my family, some members wear glasses and I'm very observant so I always notice when they switch eyeglasses/sunglasses, etc. One would think Bob's daughters would know exactly how many pairs their own dad had/wore.
If indeed as you say, Bob only owned the one pair and that one went missing, then yes, I would speculate that he did not go off on his own that morning.
However, as I say, I think he owns more than one pair, and the fact that he left his slippers at home suggests that he wore his sneakers out. Did LE mention whether they found the sneakers he wore often? Even if he had more than one pair, most men I know don't rotate sneakers (as I do to keep them from stinking up, I wear a different pair each time I workout, lol but I'm aware that most men don't do that)...So if the typical ones Bob wore are missing, then I'd say he had them on and this would give credence to the fact that he might have been out on his daily walk.
Re: cul-de-sac street where Bob lived. It's possible that he didn't just walk a straight path. Perhaps he walks not just up and down the block as was suggested in the episode, but rather around the corners of blocks to enjoy different scenic routes. I know when we go hiking or even just to the parks, we take different routes so as to diversify the scenery and explore...It would be nice to know Bob's general walking pattern(s). Too bad he didn't seem to have a walk buddy...
If Bob walked a non-straight path, I could see someone who might have purposefully parked away from his home waiting for Bob in order to do him harm...Who would know he walks that certain path but someone close or who's been stalking him, I gather. I'm still thinking it HAS to be Jeff, or Jeff's son. Jeff already was scheduled to be at Bob's home for repairs on Monday, and apparently Jeff's son has no job so he has plenty of time to stalk/abduct Bob.
Re: Josie. I also did speculate in my mind's eye that Bob's abductor could have been the barber who got angry with Bob for getting married to Fontelle because she had fancied marrying him herself so she could get a hold of all his $money. That in a sudden fit of rage, whilest trying to express her emotions to him, killed him because she couldn't have him. But then cops say Josie had an alibi, so that eliminates that theory.
Re: Fontelle. It would appear that she might have been one of the very last people to speak with Bob that Monday morning. I'd like to know what was said between her and Bob so we can get a sense of his state of mind that morning. Perhaps she asked him to include her in the trust, etc. as it's bewildering why she told LE that Bob was arguing with his daughters over her being included in the trust when Bob did not write that down in his notes. He had only written down that he was adding her to his checking account, and for him not to jot something so important as adding Fontelle to his trust doesn't make sense to me. Anyhow, perhaps she asked Bob about adding her to the trust, and then he thought she might have only married him for his $money and along with his being fed up with his greedy, money-grubbing family, he decided to vanish/do away with himself...
Anyhow, my latest two theories are:
1) Foul play by Jeff and his son, with Julie's knowledge or planning, or
2) Bob, if he on a pair of eyeglasses, walked off on his own and did something to himself because of all the in-fighting over his $money.