The hardmoney guy I use now for my flips does this but I am not really comfortable asking him all the details of his business since I would be a minor competitor of his.I have everything else pretty much in order.

The market being crazy was a factor but also I feel that I got "comfortable" and stopped the prospecting train.Coach.me charges me around $60 a month and she checks in with me everyday to make sure I did my time block.  

If you have the proper tools in place to where you can feel comfortable making a purchase knowing it will one day be in someone else's control, I'd go for it.

If you don't feel comfortable going into this much debt, you could look at using $200,000 of the $300,000 and acquiring two $400,000 homes with $100,000 down on each, and still have the $100,000 left for "sleep well" funds.

As far as where to invest, you have to go where you are comfortable with prices.  

Then if you are comfortable with them start talking about being a private lender on one of their houses.  

I suggest meeting with an attorney that you're comfortable with in case you need to evict.

It gives me comfort to have an expert who is up on tax code and then to have myself as a checking point for them.

@Nathan Smith After doing a handful of deals directly on platforms like PeerStreet and PatchOfLand, I concluded that for debt deals, it would require too much capital (and too much time on the diligence side) to get to a level of diversification I was comfortable with.

He is holding strong on him doing NOTHING other than provide 50% of the upfront cash while wanting 50% of the assets.As a side note, he (my friend) is sitting on a huge pile of liquid assets to use towards "investing".I know he is very nervous going into REI, but if we pull this off and he feels comfortable I know we can take down many more properties.