How good of a deal would be needed to make this strategy work? 

Good luck on your journey! 

We'll likely have to look for alternatives to our primary house since we won't be moving much anymore, but I like the idea of small multis and getting a lending who fully understands the VA is certainly good insight.Thanks,Fritz 

My issue is, it's been almost 3 months and I haven't be able to get good tenant applicants.

Good you are researching this topic - I also love subject tos and have written a book on the topic.  2. 

The few people I've talked to don't really have good opinions on it. 

Proximity to Disney is another competitive advantage.As property managers, we see what’s actually booking in all the resorts near Disney - the good, the bad and the ugly.

IMO your property is not a good brrrr candidate if rents do not cover mortgage and even more so if they only cover half the mortgage. 

the ones that look good in Ohio or Alabama or whatever come with their own challenges. 

I can't really speak to how good they are at criminal records; as far as I recall it either didn't find anything, or just something minor like a speeding ticket, for both sets of applicants I ran it on.