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.

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?

RBTR is his primary strategy in DFW and can probably share a few tips/recommendations with you. 

Again, the BiggerPockets store has some books on this topic, or you can learn about it by watching podcasts, reading blogs, and interacting on the forum.

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. 

Paging @Garrett Brown our resident STR specialist - what say you about tips for lead photos on listings??

Tips for writing letters or postcards?

These are features like online renter payments, tenant portal (for payments and work orders), help keeping track of work orders, tax reporting features, and accounting functionality.

Anything im missing/have any tips for.

Quote from @John Winters: Greetings BP ~I am hoping to receive some feedback on the financial feasibility of this plan and/or some tips to improve it.