So in a way, I feel we have stood the test of time and that in itself would prove our trustworthiness per se.

We do have access to a HELOC on the property which we leveraged to purchase our current primary residence (balance borrowed has been fully repaid at this point) but we would rather not pull that lever to roll into a new property given current interest rates and the adjustable nature of the HELOC. 

The most common one is that when we get a new lease signed we are not getting the rent roll populated. 

This first property is a test case to see if I want to continue investing in CR (or perhaps mexico and belize later).

Here is the summary if you are interested.In this case, the main question is when did the investor completed his start-up phase and became actively engaged in his business.Whether a taxpayer is engaged in a trade or business is determined using a facts and circumstances test under which courts have focused on the following three factors that indicate the existence of a trade or business: (1) whether the taxpayer undertook the activity intending to earn a profit; (2) whether the taxpayer is regularly and actively involved in the activity; and (3) whether the taxpayer's activity has actually commenced.

The basic membership is an easy way to test drive the organization for not much cash. 

A lot of time and money goes into test preparation and licensing.

I have owned 3 brokerages and while the test is not super difficult..

There is also no target right in terms of an asset, and you need that.That's a fair point, I don't want to get in over my head but I would like to get some passive income rolling...I just need to know if there's any actual feasible way to get me started in this business at my income level.

yes, i knew the work part. just wanted to understand the staying in it even if paying full price. not a deal breaker for me, just need to figure out where to roll my money into to use it