I hope you tell your boyfriend/fiance all of this and soon.

I hate to be the asshole, but if I were the partner of a person in this situation, I would strongly think twice before investing my future into this scenario.

As good and understanding of a person they might be, I see this causing arguments and strife in your future life.

There is absolutely no reason why you as a grown adult should still have your parents (or anybody except your life partner) on your bank account(s).

You said it yourself, your mom literally takes money from you without asking.

To me it sounds like you know the correct answer, but just want the masses to tell you that it is okay to remove them. And, I understand. That is okay. We all need that sometimes.

1,000,000 of people live on low income. You yourself said, they are not "poor" but not "well off." They need to learn how to budget and live within their means. 1,000,000 of people don't cook lavish meals for holidays. Your parents were accustom to a certain life style and now want you to support that lifestyle now that they cannot.

Believe me, I know first hand, it is hard to draw the line and not help your parents when they need it. But, unfortunately, no matter how good of people your parents may or may not be. It is very very easy for people to get accustom to and assume that their kid or uncle or whoever will bale them out when needed. I feel this has already happened since your mom now just takes the money and then tells/asks you. And, guilt tripping. Please. That speaks volumes. Why would a guilt trip even be necessary if the request was not legitimate.

What happens when you and your future partner want to buy a house or go on vacation or maybe one of your loose their job. What happens when you are in financial stress.

I am fine helping whoever needs help. In fact, I probably get taken advantage of way more than I like to admit. But, when the line of helping and assumption get crossed, I cannot help but feel I am now being used.

YMMV

This is almost an impossible question to answer, because the ratio is going to (drastically) change based on personal circumstances.

For example, we are getting ready to buy a house, so we are overly cash heavy right now because we want to put a significant down payment on the house.

Someone who is going to retire might decide it best for them to have a heavier than normal cash position to use as a cushion.

People in certain industries and/or house owners vs renters might have different cash emergency funds based on their personal beliefs in what they will need to use it for.

All that said, I believe in a solid four legged stool for retirement.

1 - pre-tax traditional 401k

2 - after-tax roth 401k

3 - after-tax brokerage accounts

4 - cash

All of these have their pros and cons. And, those pros and cons will be different for groups of people based on their situation in retirement (not to even mention early retirement). I feel you need resources in all four buckets so that you can take advantage of those pros and cons planning for and the executing retirement.

I am no expert, but I feel a lot of people just think of the now. Taxes now. Money now. Growth now. And, that is all very important. But, you also have to plan (as best as you can) for the future and what those things will/might look like during retirement.

YMMV

Typically, HSA plans start looking really good when (a) the company gives you a lump sum of money towards your account and (b) you are already maxing out your 401k and are looking for additional ways to invest your money and shelter taxes.

Your plan (if you are correct on everything) seems fairly unique to me (not that I have a ton of experience).

The difference in PPO and HSA cost per paycheck where I work is $100s per paycheck. They contribute a large sum to our account. And, the MOOP is fairly similar.

With all the above in mind, for me the HSA will about break even. But, I am also maxing my 401k, so the HSA will allow me to "save" even more.

In your case, the PPO might indeed be "better" for you.

Like all things "personal finance" it is indeed a "personal" thing that needs to be looked at on an individual basis.

Good luck!