Our rental properties are listed as well, but those are owned in an LLC. 

For a flip, you'll want to get a builder's risk policy, which covers the property during renovations, including any damage from fire, vandalism, or weather while it's vacant.

I do know the city would like to see assisted living type property.

I have several questions - imagine being able to split up property ownership into tiny pieces or having every transaction out there for everyone to see, all secure and tamper-proof.

Remember that as a serviceman, you get excellent benefits from the VA loan that can be used to house hack and for investment properties as you can use your allotment on more than one property at a time.

But I want to get into an investment property also.

Without a financial education - it's hard for him to discern which.What he should NOT do is to buy toys or spend it on fun because it'll quickly be gone.If he was financially savvy or versed in real estate - he could even buy a small apartment complex and self manage it if he had some property management skills.Advice should be catered to him specifically though, blanket advice isn't that helpful.

If you’re planning to hold the property long-term and want to avoid potential roofing issues down the road, I would lean toward the standing seam steel roof.

I mean, once we get off-market property and do some rehab, we can force appreciate it, but what about the later natural appreciation?

Allow a pets and I think you will have a great spot.Would adding that extra space/ spending that money be reflected in an appropriate increase in the property value too?