I would love to figure out how to make it work for some of the clients I sell investment property to that plan to self manage but need a back up plan when they travel for a month or two at a time.

https://www.biggerpockets.com/storeFrom more of the development and attitude aspect, below are  a couple I'd recommend: The One Thing Zero to One 7 Habits of Highly Effective People   How to Win Friends and Influence People Awaken the Giant Within How to Stop Worrying and Start Living 10XGrit 

Figuring out ways to not only hack credit cards for travel, cash back and credit scores.

Most of these things you won't be able to force him to fix..... the issues sucks but its not a code or safety/habitability issue.Pests....depends on your lease and time frame.

In Fact,   my travel expense in 2018 was 90k  -- all of which would go away with a Vegas  property. 

Note: If you go to the same meeting each month, you can do detail tracking for a month, and can use same detail to estimate expense for rest of the year.( If nothing changed)2) Meals when traveling away from home - 50% is deductible unless the meal is provided to the general public (like Open houses) than it is 100% deductible.

Should I be traveling constantly?

There have been some studies done in high vacation traveled areas such as Sonoma and Napa.

@Camille JohnsonHi Camille,Not everyone is suited to be successful at every type of job.Personality type, lifestyle choices, daily habit choices, personal goals, likes and dislikes all come into play.Not to say he can't or won't be able to do it, but a good first step might be to explain the whole thing to him.Explain all of the good and the bad points of it, and what type of effort it involves and see if he is interested.If he's not, then ask him what he wants to do, and if it's different, be supportive of that goal.Good Luck! 

I might travel down to Marion County or head out east towards Allen County.