My first reaction is that some of the sentence structures were confusing to me. For instance, "I received a public education..."

Have you thought of changing things around a bit to something like "I received a public education, while my parents used the money to fund expensive vacations. I was left home with a babysitter."

I personally suffer from the run-on-sentence disease, so it could be that I'm being overly sensitive.

I also found "He always told me..." sentence tricky. I think the problem is a dangling participle or misplaced referent, but this is the part of grammar that I can't usually name, just notice. Again I think a rewording would easily fix it, or breaking up the thought into two (or more) distinct sentences.

I'm not sure I'm hooked yet, and in a short story under 2k words, I think the early hook is really important. Is there a way to get some forewarning of the pending issue here?

You are trying too hard to build sympathy for the MC. IMHO it could have been accomplished with a few short sentences. Then there would be room to introduce plot-conlict.

Is it Uncle Connor?

Send it over.