This would be the first time I'm using a HELOC on my primary ($250,000 line) to try and obtain another property.

Now it wasn’t all the money I needed but it was close, or atleast at that time I thought it was close.

I have seen a few try to get started over there last several years, but none seem to have survived (or are really bad at SEO and marketing) since I was not able to find any the several times I have searched.That being said, I know Cadre has launched a secondaries market for their own investment offerings, but that is limited in scope to Cadre positions, and is currently closed anyways and will be "re-opening soon". 

I do my placements and turn them over at lease renewal time, but not many would want to do all the work.

Please be gentle; I'm new at this and it's pretty complex :)Structure / Legal Details- we'd establish market value through a combination of comps from local real estate agent and an appraisal- attorney would establish all required "arms length" aspects including a mortgage at a minimum standard federal rate- LLC would pay us back based on a standard promissory note over 30 yrs Pros of selling to the LLC (I think)- A sale now would be the only time we'd be able to take advantage of the cap gains exclusion on this house bc we won't qualify for the "live there 3 of 5 years" rule due to the timing of our lease and our last time of residence. 

You will have more wear-and-tear, simply because someone is occupying the house all of the time.

You mentioned a couple times that you had "feelings" of some sort about these people- reacting to your feelings when screening tenants is a good way to get caught up in a fair housing case.

They take more time, energy, stress and definitely more capital. 

First time buying an investment property.

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