At his age, he’s probably not looking to 1031 exchange them into more property and wouldn’t want to deal with capital gains unless he needs to and doesn’t want to be soneone’s note holder on seller financing.Then again, maybe he just likes hording hard assets, like the rarely used car in the garage.

If you're doing larger multifamilies and apartments, most HMLs that I've seen will not lend to you unless you (or your partner) has experience with the same asset types. 

Your biggest assets in your 20s are your time and energy.

This may include such things as paying the property taxes from the IRA and obtaining annual fair market values for reporting purposes.https://www.irs.gov/retirement-plans/retirement-pl...

Yes, I will definitely be honest when answering any questions, don't want to end my career in jail :)  I'm just trying to strategize and figure out how this approach will impact my ability to obtain loans.  

In preparation for that moment I would recommend evaluating/analyzing the investment to better understand what is required.I believe that Opportunity Funds will present a rather large incentive to those wishing to "cash out" on their investments by selling their assets and exchanging their proceeds into a qualified opportunity fund.

And of course don't forget that over the next few years you'll be adding to that depreciable basis as you develop and put the new assets into production.

The reason lenders require you to put 5% down on a primary is because you are more willing to fight for it and it'll be a more important asset to you if times get tough.

You want to get the maximum deduction possible when you buy a business asset (computer etc) by deducting it in the current year, not amortizing the asset.

It seems like it is a liability rather than an asset.