If the wall is not bubbling it's really hard to tell without a moisture reader.

For example, a broken fridge door, broken window, holes in walls…Normally I would repair it but what if it’s becoming a constant thing?

Be a fly on the wall.

Change the carpet, paint the walls etc and do it again for another 5-8 years! 

A lot of these properties I'm looking at, are mainly just outdated ( Fixtures, cabinets , older appliances ), needs carpet replaced, most have wall paper on the walls , needs an updated paint job both inside in out .So not really things that make it un-liveable , but just mainly need updated Which brings me to ......

the numbers didn't work when i went to refinance, so I sold it (as @Jaron Walling noted, it turned into a flip.)  

The better built one (concrete pilings/floors/walls) was the higher one by $12k!

You could also try leaving 1 garage and making less massive master suite but check local code on shard wall with garage. 

I now house hack a duplex and my partner hates having the tenant sharing a wall with us.

Quote from @Jaron Walling: @Jeff Gammon Welcome BP and welcome the journey!