While I do think that there are a lot of reasons to remain cautious and underwrite as if there will be an adverse cycle during the life of any asset acquired today, I think the long bull run in income property has a lot of runway left in a lot of geographical areas.Your family is smart to save some dry powder to take advantage of opportunities, but I suspect that if they are waiting for a reset of pricing and an opportunity to buy at a discount to today's pricing they'll be waiting a while.A key difference between you and your dad is you have a lot more time to make your money back if you get into the market and subsequently get wiped out. 

Not only should you lose your license for doing so, but you may be an accomplice to any crimes committed with the information provided.

I still plan to be an all cash flipper if I can.

No Starbucks coffee.

If you ended up with a an interest rate 1% higher, that would be an additional $22/month cutting into  your cash flow.  

I have always had a passion for RE and have been looking for the time to jump in, now is as good a time as any I feel.My background is in Asset Protection and with that, I am very analytical and would undoubtedly be an asset to the numbers side of the game.

@Mathew Wray coffee sometime?).

I have taught myself a basic but great amount of knowledge on what it means to be an investor.

Be an innovator not a copy cat and reap the rewards, or endure the failures.

Maybe try multiple forms of communication or offer to meet to have a coffee?