If not, the goal is that my marketing efforts will be bringing me leads like this one on a fairly regular basis (even if not as frequent as I'd like right now)

Others are irregular, but frequent - routine maintenance, snow removal, mowing.If you're looking at a 24 unit apartment building, 50% of rent is a pretty widely used number.

I am also in the military and move frequently as well and I have found it useful to know the market first and areas of interest or to avoid before investing in a rental and not the other way around.

Perhaps those lenders don't work with investors frequently.  

They knew I was 100% involved in the property, and unless I'm a loser will keep it better than a remote landlord who never sees it or is too far to make frequent visits.If you plan to only use property management, then it may be better to no occupy.

Even in areas of the country where they are supposed to be close to market value, they aren't updated frequently enough and don't take into account any condition issues or recent upgrades.

Listings stay on the market for only a day frequently and they often go for well above listing price.

That way at least you start learning and getting paid for it.To give you an idea I get asked frequently to learn about commercial.

Ask for a manager. 9 times out of 10 they have a stack of cards from contractors that frequent the store. 

As someone who frequently lends hard money, I have no problem with another investor stepping in the shoes of the original borrower if I feel they can get the job done.