Evaluate the downside of both markets.  

But I'm also assuming there are a lot more downsides to this than I am foreseeing.

We need to hear the downside.

There are of course upsides and downsides to every market but I tend to find that college towns usually have solid fundamentals, companies moving to the area, population growth, etc.

When it comes to resale and financing though it may be trickier since some lenders prefer properties that have their own separate parcels and a traditional buyer may see it as a downside when you go to sell. 

The interface is user-friendly, and the reporting tools are especially helpful for tracking property performance.One downside is that it can be a bit pricey for smaller portfolios, but the features have been worth it for me.

You rent to these people knwing their past history and something bad happens, and you will be on the hotseat.As I understood your first post, you are a fun-seeker, looking to move towards your goal....adding significant risk like this may/may not help you move faster, but the downside is the risk.Chasing the almighty dollar as a primary course of action is usually a not-smart move....take it easy, take it slow and chase fun.

.: I'm very new to this and would love to get your thoughts on this and are there any downsides to the process?

Hey @Saurabh Kukreja, we use QuickBooks Online for all of our Clients (REIs) and I use it for my personal businesses/rentals as well.We've found it has superior reporting features, integration features, and is overall more efficient to work within than other REI-specific software.The downside is QBO is not set up for REI so you'll need to do that or work with an expert to ensure it is set up for your business appropriately.

The only downside is that you'll need an account, and they lock you into a contract.