MIchael, your ramblings are often better than others’ well prepared essays. What you say about Cicero’s letters is exactly what attracts me to them. You are of course right about Pliny – his letters are a literary genre and well worth reading, but not what I’m looking for right now (they remind me of a modern literary blog).
I’ve read a book or 3 of Livy. Not sufficient motivation for me to return to him.
What are your thoughts on Aulus Gellius?
Cicero and Caesar as men of letters, sample.
Cicero to Quintus, II.16.5 (letter #20 in Shackleton Bailey, Cambridge Classical Texts). Cicero is anxious to know from his brother, who is serving as a legate to Caesar in Spain, what Caesar thought of his (Cicero’s) verses (De temporibus suis):
Scr. Romae ex. m. Sext. an. 54. Marcus Quinto fratri salutem. Cum a me litteras librari manu acceperis, ne paulum quidem me oti habuisse iudicato, cum autem mea, paulum … Sed heus tu! celari videor a te. quo modo nam, mi frater, de nostris versibus Caesar? nam primum librum se legisse scripsit ad me ante, et prima sic ut neget se ne Graeca quidem meliora legisse; reliqua ad quendam locum ῥᾳθυμότερα (hoc enim utitur verbo). dic mihi verum: num aut res eum aut χαρακτὴρ non delectat? nihil est quod vereare. ego enim ne pilo quidem minus me amabo. hac de re φιλαλήθως et, ut soles, fraterne.
Cicero and Caesar as correspondents, sample (of many letters between the two that are attested, three survive from Caesar to Cicero, three from Cicero to Caesar).
Cicero to Caesar, Epistulae ad fam. VII.5 (#26 in Shackleton Bailey, Cambridge Classical Texts, and #20 in the green-yellow Cicero Select Letters). Cicero recommends C. Trebatius Testa to Caesar:
Scr. Romae m. Apr. an. 54. Cicero Caesari Imp. S.D. Vide quam mihi persuaserim te me esse alterum, non modo in iis rebus quae ad me ipsum sed etiam in iis quae ad meos pertinent. C. Trebatium cogitarem, quocumque exirem, mecum ducere … totum denique hominem tibi ita trado, de manu, ut aiunt, in manum tuam istam et victoria et fide praestantem. simus enim putidiusculi, quamquam per te vix licet; verum, ut video, licebit. Cura ut valeas, et me, ut amas, ama.
Re Caesar:
Brutus.
Ha! who comes here?
I think it is the weakness of mine eyes
That shapes this monstrous apparition.
It comes upon me. Art thou any thing?
Art thou some god, some angel, or some devil,
That mak’st my blood cold, and my hair to stare?
Speak to me what thou art.
The Ghost of Caesar.
Thy evil spirit, Brutus.
Art thou some god, some angel, or some devil? Shakespeare got it.
Regarding his writings (specifically his commentarii), there is the Caesar of Mr. Chips and schoolboys, and there is the Caesar of serious adult students of Roman and western history and its outsized historical figures (especially, like Churchill, of the few who could write as well as act).
As Mr. Chips, Barry, you must have had your fill of Caesar 
. Maybe of Catiline too. But how about a stew of Cicero’s epistulae and Caesar’s commentarii from an adult perspective?!
He’s a one-man Wikipedia. I’d rather read Leofranc Holford-Strevens.
If you still haven’t read the Iliad and Odyssey, you must do that before anything else,
And thanks to Randy for the epistolary excerpts. I again laughed out loud at Cic’s oh-so-true ego enim ne pilo quidem minus me amabo.
I read the entire Odyssey in graduate school in a 10 week period back in my grad school days, and have revisited it several times since. The Iliad was the problem, and I’ve more than half filled that hole now. No need to go quite so quickly as with the Odyssey, thankfully.