The pitfall potentials are many, and most speak back to neglect in process.

Your designer should be able to determine and understand your ideal guest, and curate a space that speaks directly to the clientele you want to attract.

Generally speaking, have any of you invested in this area and been successful?

That said, everything I read and Realtor friends I speak with confirm that sales are far and few between in residential housing at the moment. 

You're only limited by your beliefs.Practically speaking though, 2-4 unit multi is very very doable starting out, especially if you are willing to owner occupy.

That'll help you figure out what direction to aim in before speaking with a bank to figure out how much you can qualify for. 

Hello, I have been speaking with an investor who would like to partner with me on some future real estate investments.

Speaking of which.. what’s your plan if the property needs more updates than expected..would you hold it longer, or look for other creative ways to make it work? 

I go to vacant properties at least weekly unless they are multi-family with active neighbors.)Generally speaking, if a property isn't moving (and others in the area are), either you are priced too high or there is something lacking with your property.

I recommend speaking with a tax strategist to discuss options to reduce your tax liabilities without becoming an S-corp.