I was raised frugally, so I spend little by nature.

It's just human nature - we tend to attribute characteristics we like to people we like.

It is possible there is a stipulation in the current plan that delays entry of a new employee into the plan for a year of service (or something of that nature). 

Part of the process of the BRRRR strategy is the refi portion to get you back some or all of your initial cash invested so you can keep going but not all properties will be in a position to get the refi so that is something you need to consider with your lenders and you should have an alternative for that instance.

(On-base housing and food can suck, but it's way more affordable than the alternatives!

More from the rules in regards to advertising “All advertising, regardless of its nature and the medium in which it appears, which promotes either a licensee or the sale or lease of real property, shall conform to the requirements of this rule.

Naturally the best thing to do is ask him what he prefers. 

Given that, I'd say, ensure that you have a well diversified portfolio that includes everything: Wall Street investments, and various type of alternatives in real estate and beyond. 

But, if you need to meet with someone for an hour or two during the day, and know in advance the day and time and need a professional environment, they provide a nice alternative.

If you take the self-management approach, there are definitely some tools that can help with managing things moving forward but my natural assumption is that no matter how easy the on-boarding is, tenants will probably still want some sort of hand-holding through that change management process.