These are two different questions. One is about immigration and customs at entry, the other is about pre-flight security.
On customs and immigration, your electronic items are not a problem; probably no one will even look in your bags unless you get sent to a secondary screening for other reasons. However, if you are searched by customs, it will look like you are entering for work purposes. Be sure you have your story straight about why you have each item. "My boss might email me" is not going to cut it for having so many computers. If, however, you really are entering for work, perhaps as an IT contractor, it is not unusual to have numerous computers.
TSA will not inspect your hand luggage prior to entry. Your local airport is responsible for this. Sometimes additional contractors are employed at the gate to 'double check' your baggage to TSA standard, particularly if your flight is operated by an American carrier. This procedure is annoying but basically pointless. If you use a non-American carrier it rarely happens. Anyway, the general rule is that your items should power up and work. Individual hard drives do get a lot of scrutiny but they are usually allowed to go through eventually.
On domestic flights and your exit flight, of course TSA will check your hand baggage. Same rules apply really, just make sure it all works and you know why you are bringing all these gadgets.
You should split your electronic items out amongst as many trays as you can; it makes it easier for the xray operator to see what's going on and therefore less likely to attract operator confusion and a time-consuming hand search.
If you really need these electronics with you, do not put them in your checked luggage. It is wise, in my experience, to assume that your checked luggage will go missing! (I lost three more bags last year ...)