There is so much that goes into buying an STR, especially your first one.

@David YoungRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Has anyone joined or spoken to Carson and Jackson Weiner about their mentor program to buy/sell land?

Shane, buying "subject to" in Illinois is possible, but the state has stricter regulations around real estate transactions.

I would focus on systemizing property management as much as possible so adding more units becomes easier over time.If your goal is to buy one property a year, then stick to your pace.

If you are getting buying now in TO & Niagara, you will need to have a large down payment for the units to cashflow. 

Investment Info:Single-family residence buy & hold investment.

-With my current role in my career and trajectory, I will be able to make the move out of midland in 1-2 years, so I would love the ability to leave and not worry about my home sitting on the market when we are trying to buy a home in Austin.Those are some of my thoughts and I would love to understand the reasoning for/ against this.

I’m based in Fayetteville, NC, and I’m looking to get into buy-and-hold real estate investing.

I’ve done 4 cash out refis to buy 14 houses basically for free, since I didn’t have to come up with any out of pocket cash for my 20% down payments on the new houses.