bulletpruf,
Sounds like you're building up quite a collection, and trying to cover all the bases. There's nothing wrong with that, many people who think about these things tend to do the same thing. However, speaking as someone who's "been there, done that", I do have a few suggestions.
#1 - In my ratchet universe, the roto-head (swivel) reigns supreme. It won't do everything, but it does most things - and does them very well. My concern with your roto lineup is that you are choosing the worst of the rotos (Harbor Freight) to fill this important category of ratchets. The HF rotos have really terrible backdrag, are annoyingly loud, and can't be disassembled for cleaning and lube. In a stubby roto, HF is about the only choice - but for a normal length I would suggest that you at LEAST step up to Kobalt or Husky quality, and definitely shoot for Carlyle or Snap On quality if you can afford it. I am worried that if you only have HF rotos to mess with, you won't end up liking them or using them much, and end up not enjoying all the benefit of these really excellent ratchets.
#2 - I've bought a lot of ratchets that have "overlap" in functionality. This is really money wasted, although I've learned a lot from it and I can always recoup some of the cost by selling extras. I would suggest this as a strategy to avoid this:
Think of what each size brings to the table, and select ratchets accordingly.
1/4 is about finesse and working in cramped or inaccessible areas for the most part... and small fasteners that are removed and installed rapidly. The Roto ratchet really shines in 1/4 drive - I'd pick up a good quality standard handle length roto FIRST for this drive size. I would then choose a long handled like the TLL72 or equivalent for reach, a stubby of some sort for super cramped spaces, and finally something like the Armstrong MAXX for angled work where you need a stable socket that won't flop around.
3/8 is the general-use workhorse. For anything involving somewhat "normal" sized fasteners, you will use 3/8 drive the most. Go nuts with it - buy every conceivable style you find a use for. I'd start with a quality roto, an Armstrong locking flex, a long handled, and a fixed and flexing stubby. Add as needed. I don't really consider any of my 3/8 ratchets as "extras" or unnecessary... they've all come in handy in some situation or other. It's up to you to decide, based on the work you do, which ratchets will be the MOST useful and obtain them first.
1/2 is about power. I don't own or want a roto in 1/2. I don't want short ratchets in 1/2. Ideally, a long handled fixed ratchet, a long breaker bar, and an Armstrong MAXX locking flex is all I need or want in 1/2, but I've piled up a bunch of other 1/2 stuff over the years that I never end up using. Such is life.
#3 - Non-locking flex heads and roto-ratchets overlap a LOT. No real sense owning a bunch of both in the same handle lengths - decide which style you like best for a given length and drive size, then ontsin other needed ratchets instead of redundancies.
In any case, buy what you want... just give it some thought and read as much as you can here. There are some really great knowlegeable folks on this forum!
Happy ratcheting!