Jump in and learn and get started even if we lose money?

[Ryan Detzel]

I've been researching buying something for years (about 4 now) and have yet to pull the trigger. There is always a reason and in my area (Massachusetts) prices have stayed very high so that makes it worse. My wife also isn't full onboard as she's very risk averse and she's worried that if the property needs work or is far away my time will be stretched even further which isn't great for the family. 

Anyway, because we know nothing besides what we've read, because we're always talking about the "What ifs", I'm ready (and I think I convinced her) to just go for something that we feel safe owning, that's easy to start (low maintenance) and by my calculations at most we'd be on the hook for maybe $4k/year if renting didn't go so well. This is by far my ideal purchase but I feel that since she's interested in it, that might be a good way to get our feet wet and help us understand everything before jumping too far in. 

As long as we can limit our risk is there any problem diving in like this knowing that there is a chance we'll lose money?