We'll give them an extra cushion just incase the market continues to fall.

This way you have a decent cushion if you underestimate on some of your numbers.I would encourage you (as Brian does) to find a GC to work alongside you (unless you are a rehab king).

I figure if I can get anything at a 10% discount, that's cushioning for a potential 10% pullback in values.

You have to put feelings aside and see this as an opportunity to get rid of a problem and get the property ready for a brand new tenant.Consider the cost of opportunity of one month rent vs not getting these tenants out.I am assuming you have some cushion funds and can weather one month rent.

I usually only share with a select few in my circle because not everyone is supportive and/or understands the concept of escaping the "cushion" of corporate life and still achieving your goals.

It seems logical to use conventional loans in the beginning, the low interest rate gives a softer cushion for errors (which i will try to avoid).  

That won’t help with cushioning or heat retention though- I’d recommend a waterproof underpayment like pergo gold for that.

Yes, the price of the property is a big part and your fees will have to still make it a great deal but enough cushion in case the buyers need it lower.  

Also I hate to mention this but if you happen to get injured you could end up losing your scholarship for athletics if you can’t play anymore so having a cushion for undergrad is a good idea too so that you can finish your education.Also considering your age 5 grand is a lot to spend on an engagement ring.

So it would basically require the hard money lender (who has about $30 million in loans) to go out of business AND the underlying property not having enough equity cushion in it vis a vis my loan for me to lose principal.