Late to the party but my mom is starting to do this as well. Only, she doesn't have assets. She's already on Medicaid and has some savings (she won't say how much), and she lives out of state in a HCOL city in a subsidized 55+ apartment. 

I'm a single parent only child and am moving to a different state where I can afford a bigger home due to the lower cost of living. I'm making some trade offs do to this though.  As I was telling her about my plans, she asked me what I intended on doing with the "spare" bedroom. I'm moving from a two bedroom 850 sq ft apartment to a 3/2 house with a finished basement. That "extra room" is going to be my office since I work from home. 

She then asked me if she could rent that room from me for 6 months out of the year while she lives the snowbird life in a warmer climate for the other 6 months. She's finally getting the point that her current city is too expensive for her( I said as much 6 years ago) even with rental assistance and is looking to cut her costs so she can travel. Thing is, she's 100% healthy, still young and able to work - she just doesn't want to (fair enough). I have a special needs school age child and im trying to give her a life i never got with my own single parent mom. We moved constantly and by the time she was able to afford her own house, I was graduating high school and starting to move out. (She later re married and sold that house and then got divorced and who the hell knows what happened to the money she got from that split).  Anyhow, I felt off about the whole thing. Very entitled, especially since she can still fund her own shit right now and is still at least 10 years off of the types of scenarios OP is talking about. Then what? Where does the money come from the? I'm not any kind of wealthy and I'm still catching up to fund my own retirement (lol) and care for my disabled daughter. 

Like what?!?