I fly down several times a year to attend events with Lifestyles Unlimited to hone my real estate investing skills. 

I was seriously in debt, trying to live some kind of fake lifestyle where it looked like I had money even though I didn't.

Depending on your investment plan, Lifestyles Unlimited may be a good fit for you.

I wanted an area that had a long track record of steady job growth, growing population, out of staters consistently migrating there for lifestyle/jobs, good balance demographically (types of workers, age of residents, etc.).

In my town, upstairs laundry is a life-style thing.

They have some premium/enhanced services for a small fee.

I am working towards the goal of a lifestyle of all passive income or property management type work and i am just wondering if I should be asking for more or if there is any better ways people have come up to structure deals with their families or from other people providing financial backing in this industry.

Sounds like you are maybe getting close to a full time or part time employee - give them a truck and small hourly - maybe throw a plow for winter on it and a trailer for summer grass cuts -  maybe it can make sense for you.I have always had a property management company (owned) and used for another real estate to manage my property - this is a full-time lifestyle for me now, so no capacity for self performing tasks.

I just use the famous phrase: I'm living these years like you won't, to live my later years in a lifestyle you can't. :)

Just depends on current job, life style, interest in real estate, etc.