I've noticed that properties with virtual tours tend to get more engagement online, and investors/agents who use them often say they help attract more serious buyers and renters. 

In my opinion, an in person meetup > an online connection.You may want to consider making a connection here and meeting up for coffee or attending a real estate networking event.Best of luck!

He can spend the next few years-ish getting a finance degree through an online school while working part time, but he just got offered a full time position helping with sales for a local wholesale real estate company. 

Cold calling is a great idea to get started, but maybe try connecting with local real estate groups or online forums too—they can sometimes have off-market deals.

When researching online, it looks there are some instances where non-vets can assume VA loans, but the veteran's entitlement would remain tied to the loan.How common is this and are there ever situations when this a win-win for both sides?

Here's a list of things to track:- Formal lease application- Formal signed and executed lease specific to your state- Payment history (I recommend using online rent collection like Apartments.com, RentRedi, etc)- Maintenance requests and receipts- Accounting for all rental-related expenses (repairs, utilities, etc) The more you treat it like a business, the more helpful you are to your CPA come tax time. 

Historically used online software without much issue.Now that I'm looking at the settlement statements from 2004 and looking at a sizeable depreciation recapture hit, I came across a number of questions / issues:1) I believe in 2010 I incorrectly set my basis (I did not include the parking space and upgrades to the units - granite, flooring, etc.).

Also just look online and steal some ideas...I used to Google Luxury Kitchens and then figure out how to do the same for less $$.You'll be fine with your experience.

Could not find much online so figured I would turn to BP.

I came across one of these loan agreements online somewhere a few months ago, can't recall where I found it but it was clear in reading the loan agreement there was no language referencing the loan actually encumbering real property, it was just an unsecured loan.