I don't know 100% if this is the smartest decision or best decision long term, but that is why I am here trying to learn and understand. 

How much will it add to the homes value in the long run.

As long as the note is recorded against the property.

Why do you think purchase contracts are so long and have such small print?

This would have to be retroactive to the date of her Active Duty enlistment (or orders if guard/reserve) and apply up to 6mo after her Date of Separation.It can be a long hard road, but well worth it. 

Are you looking for steady rental income or long-term appreciation?

Rents per unit are about 1K for long term tenants, although I'm likely to do STR or at least a combination of the two.

I own and manage a short-term and just finished with long-term in Seattle (Belltown & N Beacon Hill) and also a real estate agent.People with skills are always in need, for sure.

When you reach your goals wouldn't it be a necessity to have your health so you can enjoy your achievements for a long time with your loved ones?

I grew up in the suburbs of Chicago and would ideally like to invest in IL since my family is still there and can serve as a home base for whenever I need to be in the area, but with IL property taxes being as high as they are I'm also scoping other markets in nearby states.Does anyone have any general advice for buying / investing long distance?