This sounds familiar, and according to some threads on forums.ea.com, others will think so as well.
I think I have had this with Part's 2 & 3.
I'm sure you have solved it by now, but someone else might find this useful?
You do not only have to look for him in your Springfield, you can look in Other Springfield as well, I have had most success there.
You are not restricted to how many times you tap him or attempt to on any day, but you are restricted to one find per visit.
Other Springfield is, I understand, a town built by EA on the servers and is slightly different to friends towns.
I assume this was done in case there are no friends so everyone can still do quests.
I read Bob could appear near Squidport or Springfield Heights, though I have never seen him.
The only times I have seen him is at the entrance to the Sprawl-Mart or running around town, sometimes running in front of me even as I was scrolling away from him.
When you tap him return to your Springfield, by that I mean actually into your town, I don't think it matters how long you are there or what you do, but I always collect taxes.
Return to Other Springfield and do it all again.
He is quick, so if you miss him you have 2 options.
1st. Return to your town then return to Other Springfield.
OR.
2nd. Scroll backwards and forwards from one end of town to the other like ploughing a field, even if you don't find him you might see something interesting.
I always start from the sea and scroll in columns, keeping parallel to the sea and working inland slightly overlapping each time, you can use roads as a guide.
Because I have seen him in built up areas, never the woods or Camp Kruaty, I've always found him closer to the coast.
If I don't find him, I then search rows keeping parallel to the mountains but using the same technique.
If I don't find him, I either repeat all that or search Springfield Heights, then Springfield again, at this point he sometimes reappears.
Or just do it again.
I don't know if he came out of hiding or if he had been running around all that time?
When you have found him the specified number of times you will not see a popup notification in Other Springfield, you will see the popup when you return to your Springfield.
It will tell you, you have completed the quest, give you some money and xp and show other characters that you can get that are like him, I think it's his family?
As for when Part's 2 and 3 start, I read that is randomly generated.
Pedantic and detailed I know, but that is everything I know.
If this has helped you, please consider leaving some xp. Thank you.
