Is my friend outrageously entitled in her expectations?

She won't get one if they are for the disabled - does she want you to lie and say she has a disability ? She would need much more in the way of proof, my son lives in purpose built accomodation for the disabled and it took years of negotiation with the Health and Social Care Partnership

No harm whatsoever in wanting what she wants. No harm in asking for it either. Very few people get what they want in life because they're the most deserving of it, many enjoy their lifestyles as result of a combination of luck, taking advantage of others and pushiness. The difference tends to be that they call it their career.
I very much doubt how ever firmly she asks or what she spins she will secure a bungalow designed for a disabled person unless she can prove she has a disability. The exception may be if (as in my town) the number of this type of property is higher than demand, so they may be more flexible and she may drop lucky. Its no harm to you either way and if you don't want to help her, just tell her no.

Yes but not if we are using taxpayer funded resources that have been allocated for a vulnerable group. No decent person takes that route to getting the home they want.

She's just one of life's takers who has never taken responsibility in her life.

Her previous lifestyle sounds amazing.

But please don't assist her in gaming the system to someone else's disadvantage. Especially when she has contributed so little herself ( teaching period aside).

First post nailed it.

she sounds unbearable, to be honest.

This, I don't see what you'd actually be doing?

I also don't get OP's outrage at someone wanting to live in a particular type of property, don't we all want to be able to choose where we live?

Wow, people like this really make me wonder why I've worked my nuts off over the years. She's a proper CF.

she's prepared to elbow someone disabled out of the way if she can.

She will have a lot of trouble trying to convince any LA, that her housing needs are based on disability, if she has no record of having any. They require proof!

Very laid back, getting by on benefits and subs from friends and family

Run far, far away. Once you take a step back, she will move onto the next person.

Just nod and smile and don’t get involved

She sounds younger than her years and with a poor insight into reality, to be honest.

If I was in your shoes op I think I would keep in touch with this woman just to satisfy my own curiosity about how things work out for her.
BUT, I would also swerve and dodge, duck and dive, make sure I never actually do anything or put myself out or expend any effort to help her.

This. I used to work in housing and properties suitable for those with disabilities are always in low supply and high demand.

In my life, I have noticed a high overlap between benefit freeloading and 'alternative free spirit types'. They are all perfectly capable of work but do somehow feel entitled to no work and take the money from those who do.

There are so many people playing the system and she’s just one more. The problem is, it’s hard to respect or like people like this. I feel for you. You find her interesting, she’s unusual, but there’s a drawback to her lack of honesty, which leaves a bad taste in your mouth. If it were me I’d have to refuse to help, and explain I’m not comfortable with dishonesty.

She sounds unrealistic rather than entitled. But then you appear not to like her very much so I guess you'll see whatever she does in a negative light.

She's not going to be considered for a two bedroom place so she's wasting her time. She'd be better off finding a one bedroom with nicer neighbours with scope to divide either the living room or bedroom so she can have a separate space for her hobbies. I don't see how you getting involved in the application would change anything, unless you're an MP or such.

Why would you want a 'friend' like her?

Good on her. The benefits system encourages you to grab what you can. If a million people per year from overseas can play the game, why not her?

And to answer your question yes she is entitled. I’m sure we could find some profound piece of learning in relation to “ reaping what you sow” that would be applicable in this situation.

How does a person assist in these cases anyway ? Are you just helping in a “friend” capacity or do you actually have a connected profession that she’s relying on?

I’d say nothing but decline assisting with her housing situation in any way.

As someone who part bought a property designed for disabled people I highly doubt she will get one without significant medical evidence.

We had to provide evidence of all diagnosis of medical conditions on NHS headed paper, NHS OT reports and disability reports before we could even be considered to part buy a house built for families with a disabled person in it. All the local authority disability houses in my area were allocated to families with children who had a disability or who had a parent with one. They can't allocated disability houses to people that don't need them.

Just don’t get involved. We get loads of these sorts down in Devon and Cornwall. Have been off freewheeling through life for decades, picking a bit of fruit here, selling some hemp bracelets and incense at a festival there, doing the van life thing, and now times are harder and they want somewhere to pitch up, but it has to come with all these requirements, sea view and close to the beach, nice sunsets, dog friendly, free electric and water, etc. A lot of people are ageing out of that lifestyle and especially with cost of living, it’s not easy to have no safety net and to be too old for seasonal grafting. I personally would just nod and say good luck. But don’t get involved.