If you don't fully understand the investment, do not invest. 

It's really important to understand the difference.

I'd be willing to live in it which appears to have some benefits for a condo conversion depending what town you're in.The thought being that we could buy a duplex/triplex/quad, convert it to a condo, and sell off the remaining units leaving me with (at the end of the day) an affordable housing option.Here are the condo zoning laws that I found for Sunnyvale: https://www.huduser.gov/portal...My understanding is that they don't do condo conversions with <3% rental vacancy rate, but it looks like it was 3.1% from the most recent HUD market analysis for my area that I could find: https://www.huduser.gov/portal...Does anyone know someone who has done a condo conversion in the Bay Area?  

@Nate P.Your profile hints that you are living abroad.If you are a US citizen - you want to make sure that the CPA you work with understands the foreign earned income exclusion(FEIE).If you purchase a property and are expecting valuable feedback on how that property will impact your tax return, you will need to provide a rough profit and loss projection(rental income and expenses) along with purchase price to have a conversation with your accountant so that they can provide you good feedback. 

@Anthony Theokary Directly from the Philaelphia L&I website:  A licensed Philadelphia contractor must perform the work, except for projects on an existing one-or-two-family home that don’t require an electrical or plumbing permit.The scope of work you are performing goes far beyond the limited exception which falls within the EZ permit standards.

(even though buying something else would also put me at the same rate)My understanding is that an owner occupier would pay more for the property than an investor, but i  have leases that end in September, which is not the best time to sell. 

Then I have standard 12-month lease that covers me and my condo appropriately. 

I understand the general concept of how it works, but not a lot of the intricacies.

When talking with new and aspiring private money lenders, I always recommend getting added as an insured on the borrower's property hazard insurance policy (known as an insurance binder). I had a new PML ask me about ...

This speaks to what @Russell Brazil said about being thorough and making sure you understand what needs to be done.I certainly agree with what @Bill J Fay said about the before & after, but, if the property is bad enough, you might want a contractor for the first inspection.