Well, now I'm leaning towards buying my First Property as an Investor and then Flipping it in a 3-4 month timeframed window.

Thanks for the info guys, still leaning toward getting rid and going with a cashflowing property.

He's also offering a lean on the property (which I assume is free-and-clear, but may be worth <50k in severed+disaster scenario).

Your financing needs to fit your business plan, use of funds, allow profits, that looks a little lean anyway.If you're asking grandma to make you a mortgage at 100%, forget she is grandma and get to your attorney for an arm's length transaction, as much as it can be, You need to be more careful with family IMO than any stranger.Initially, just approach your investor and pass it by them and see what the thoughts might be, how much and interest, how long and how they get paid can be negotiated.

I am leaning towards an all cash offer contract and took the idea of cashing-out on my primary residence out of my head, taking the advice of most of the posts.

I've never heard of an employer 401(k) plan that allows participants to invest in private placements.I can have a self-directed 401(k) and I can vest investments in different LLCs that the 401(k) trust establishes, for the convenience of the trustee (me).

more affordable and still convenient to the city.

But, I do not have 3 months living expenses saved up which would make me feel a lot more comfortable.I'm leaning towards paying off some debt before I'm comfortable acquiring another property.

In my world, landlords need to just provide the method (the system) and let the tenant select what is most convenient for them.

You can lean the same things they teach on your own, a degree is just to prove to other people what you know.