Working with a close friend who is our broker and my wife (who recently acquired her real estate license).I'm paying $2200 mortgage, if I could I would rent out, I want to be certain I can make a profit as I most certainly can't afford two mortgages.

I like the rent option in this case, but I would likely look to add an additional camper pad on the land that I could rent either short or long term.

I think NC is one of the few that negotiate due diligence money to seller in addition to earnest money deposit. 

-No clunky remote with 50+ buttons that hasn't been redesigned since 2003 that guests need in addition to 1-2 other remotes to perform basic functions.

We'll both chip in equally for the costs and expenses of the acquiring the property (looking to buy an apartment with a value between 500k-600k in Chicago) and live together for a few years in it.

So the 85k property would be 43.5% of the 64k cost basis plus 43.5% of the additional $44k you invested during the exchange.

Additionally, what are your thoughts on doing a vacation rental as your first investment property?

Would be happy to connect and answer any additional questions you might have along the way!

For reference: I acquired all 5 properties in year 2020.

The key will be ensuring you have a good enough (1-1 or higher ideally) DSCR ratio in addition to a strong credit score.