I should have been chasing the the dream lifestyle.

Prefer Cape Coral or Naples area, but would consider anywhere in SW Florida if the property holds the right characteristics for my investment AND lifestyle criteria.

My blog/website is about long distance self management, landlording, investing in class A investments, investing in a transient lifestyle, etc.

My blog/website is about long distance self management, landlording, investing in class A investments, investing in a transient lifestyle, etc.Look forward to seeing you around!

Then I began searching for a Real Estate Investment Group and signed up for Lifestyles Unlimited (LU) as a recommendation of a family friend who has retired at 37 and live on passive income.

Lifestyle please such negativity for no reason.

Just from a risk/age standpoint, you can take more risk because you don't (presumably) have dependents, obligations, other costs of be a certain lifestyle (we all remember college mac and cheese days) and you have many many years of income to come; therefore, you can mess up a bit the way a 75 year old cannot just based on the number of income earning years ahead.

It takes a level of discipline that many people don't have, to avoid lifestyle inflation. 

How much you decide to set aside for wealth accumulation depends on individual needs, lifestyle, family issues, etc.

Whatever strategy you choose will depend on your current financial position, your goals, and your lifestyle.