Im just thinking about, in the event I want to move out / purchase the next property, how much I may be paying out each month to hold on for potential/eventual payoff when I sell.And how long would it take for sufficient appreciation for a decent return? 

Rul. 8429039, provided that a two-year holding period is sufficient to ensure treatment as a tax-free exchange (all other tests being met). 

This sounds like the price is too high or they have found a better deals after closer look.It really depends on many factors, like what is the exact location, what is the shape of the lot, how is subdivided,  how is it accessed, how far are the closes utilities, are those private / public, is there any public access, are the access sufficient or do you have to build a new roads etc. 

See how the numbers work that way.If the vast majority of houses are selling in the $130k range, you may have to accept that's just where the market is and pass on this deal...or get a better price...

If someone were caught drug dealing in 2010 but finished their sentence in 2012, that would give them six years of history to prove they had changed their ways, which should be sufficient for any Landlord.In your case, the guy was honest and admitted his mistake.

The vast majority of private Landlords have no clue what they're doing whereas a professional knows the law, can spot red flags, and can find you a quality renter.

This is typically handled through a rent-back agreement at PITI with a sufficient security deposit.

You do have to live in both properties as your primary residence so if you are trying to buy both at the same time this wouldnt be possible unless you and your wife were separated and living in different primary residences but if sufficient time has passed since the first purchase then you could buy another property with her VA eligibility.

Because they could be vastly different.  

If you have a lease in place and can document that the property has been vacant for repairs, that should be sufficient to count 75% of the lease income.