Originally posted by @Derek E.

Right now I am looking to add a property to my portfolio, I have been reading books and blogs to better prepare my mindset and my wallet for such endeavors.

@Candace Wiley - While you will not have to file a separate return for the vacation rental, you will have to include it on either Schedule E or Schedule C of your personal return depending on a few factors and the circumstances revolving around the services provided to your tenants.  

@Brad E. , common mistake to make to not get them signed.

If it copies the development trajectory of Chicago, then I would expect further urban growth as older neighborhoods return to popularity. 

They didn't like that payment.So- my guess is that it will have zero effect on your d/e, but they don't use common sense.  

if your an accredited investor the syndication approach is one that is quite popular.. and of course those deals the sponsor frankly is more important than the asset most of the time. a poor operator can ruin a good project a great operator can save a struggly project or one that has some bumps in the road.crowdfunding is an option one thing though that I don't like about crowdfunding at least on smaller debt deals is there is a huge heard mentality and the debt deals once posted sometimes are subscribed in 30 minutes.. no way anyone can do due diligence on those.. its like throwing darts at a board..

Now that's a popular (and difficult) question.Properties like that aren't on the MLS every day (or even month).

Think E*Trade with different paperwork capable of investing in real estate, etc. 

That same Market Analysis may show you "not" to invest where you think you want to.3 - These are not E/E Strategies.