Another part of me feels like that is still a bit of a gamble and that I may be better off working just as hard at something already proven, something where I can come in and work with others.

I work with idiots that gamble in the market as my full-time job, and I've seen people do some crazy stuff and lose piles of money in days.

So investors tend to go for the cash flow properties as the cash is more or less stable vs relying appreciation which can be a gamble

The power in your first deal comes from KNOWING what ever you did, is no longer a gamble.

Secondly, in looking at claims overall, very few losses completely destroy or "total" a property, which, if your angle is to carry what is owed on the property, in hopes the lender will be paid, is a very big gamble to take.

  " I am buy and hold forever"   "I am a Cashflow investor"  " I don't expect appreciation"  " Appreciation if gambling I am not a Gambler "  "Appreciation is icing on the cake "  these are the most common things beat into investors heads these days. and then regurgitated.. 

I'm starting to see most people seem to be playing the market in regards to appreciation, which in turn is essentially gambling in my eyes (although, some markets require it for a profitable outcome).

As has been mentioned above, the worst thing you can do in such a situation is go in being able to juggle loans (see Uncut Gems...good movie even for investors to check out) that ultimately can turn into gambling when you don't know if you're numbers are going to bear out and you're going to hit a profit that makes it worthwhile in the end.

You could attempt a lower amount ($200-225k) just off campus and try to get student rentals but might be a gamble.

Here is how my investments are broken down using approximate numbers.Real Estate= 60% reflected in equity positions (pays me to own it/dividends in the form of cash flow/appreciation)Physical Gold= 8% (hedge investment)Physical Silver= 16% (held as speculative asset with inherent redeemable value)Bitcoin + other Blockchain via coinbase= 8% (held as speculative asset-long term value unknown) I know some people will ask how I can be a precious metals bug and own Bitcoin.......The truth is that people much smarter than me have decided that it is a speculative asset class that is worth gambling on.