"Lose to win".

@Jacob CasarezI'm not losing any sleep. 

And you need to be REAL CAREFUL with what you are venturing to do, because it is fraught with risk, and I'd hate to see you lose all of that money you have made in your other successful careers. 

As an investor without large amounts of capital, you stand to lose loads of money if you try and add apples (actual, known, real numbers) to oranges (best guess numbers).

The best case scenario for someone who's not a young gun looks something like this in my mind:You have cash tucked away to cover:Downpayment6 Months of mortgage for the new property (in case of vacancy)6 Months to a year of salary put away in case you lose your jobAlso, you'll have a solid W2 job with enough income that if you lost everything listed above, it wouldn't ruin you.

Main reason I'm looking to rent is because I have very little equity in this house and I would prob lose money if I sold it now once closing costs are paid.  

You may need to take out a first mortgage to protect your second, if you lose the collateral to a first lien holder, you're out of collateral.

That way whenever he finds a good deal that he needs to close asap on he will have the funds available with waiting two, three weeks to close and potentially losing the deal

You have to factor in analysis of the "hassle factor" such as flying out to view the property, time taken to do so (I don't recommend buying anything sight unseen).  

Thus began an extremely stressful 10 weeks (occurring simultaneously with losing my dad).