The truck is great for quick hauls when you didn't plan on it, but the trailer wins hands down on ease of load, unload, weight capacity and the ability to leave it behind. 

If you had the ability once graduating to make 100k to 200k a year starting out in your chosen profession that is different.A lot of people rack up student debt and then can't get a high paying job and are stuck being underwater on loans.I don't know if the area you are looking in that multifamily trades at 150,000. 2 doors would be 75k a door in price, 3 unit is 50k door, 4 unit is 37,500 a door.

Better asset protection, better discharge-ability, etc. 

As for not getting notice:  CA tax collectors are VERY clear that not getting a bill or notice does not remove the responsibility of the tax payer to pay all taxes due, in full, on time.  

The Construction Cost Index in my region has been remarkably stable, at right around 3% plus/minus a couple tenths, for decades.So I am going to say with a fair bit of confidence that the $5000 roof will cost just over $9000 in 20 years.

The technology side has always vexed me and I understand that your ability to efficiently and quickly market your wholesale deals to as many investors as possible is critical to establishing your credibility and presenting your properties in the best possible light. 

Should this deed in lieu have an impact on his ability to get a traditional bank loan for his own home? 

You then have 60 days to put those funds back in the IRA or into a new IRA or other qualified retirement plan.The old interpretation was that you could do this one per 12 months per source account.The new restrictions limit you to one such transaction per 12 months, period.This does not impact your ability to move funds from one IRA or 401k to another on a direct, trustee-to-trustee basis.  

Doing the latter means that returns are more related to the individual investor's abilities, more intelligent, experienced and savvy investors will simply blow away the average.

I am assuming the owners know you are going to rent them out, not live in all 7 houses.If you have the ability to buy them in 12 months, and they are this good of a deal, I say rock and roll!