I have found some options which seemed ideal in sync with the BRRRR method, however from looking on sites like Zillow and Redfin, there just seems to be so many available options, for nice rentals and good rates, so would it even be ideal to buy in the area if it would be so difficult if even possible to find a tenant?

While its nice to borrow as much as possible, the risk involved can sink someone as in most instances their is personal guarantees involved and lenders will bankrupt sometime to try and get every penny they are owed. 

To put it nicely, I would proceed with extreme extreme caution, if I were in your shoes. 

Here’s a breakdown to help you navigate your first deal, incorporating advanced strategies, including 1031 exchanges, to attract a broader range of investors.Neighborhood Recommendations: Chicago offers a diverse range of neighborhoods for different investment goals:Wicker Park & West Town: These areas are known for their strong rental demand among young professionals and offer good potential for cash flow.Lake View: Ideal for attracting tenants who want to be close to downtown while enjoying local amenities.The Loop: A prime location for high-income renters, making it an attractive option if you’re planning to house hack and generate a steady stream of rental income.Property Types: Opt for properties that align with your investment goals.

Works just fine for me and the solar panel can be directed independent of the camera which is nice.

If you saying you want to do this in NY is only a result of you wanting to live in NY - then consider the option that you could purchase an out of state rental, cash flow, and use that cash flow to help payoff a nice rent in NY.

You are on your way to having a nice portfolio :)

Your approach of fixing them up nice enough is one of several things some dont seem to comprehend.

It has a slightly more vacation-friendly vibe with its arts scene, annual events, and outdoor activities that draw visitors regularly.Since you're targeting STR occupancy over 50% without extreme seasonal dips, you might consider neighborhoods near popular attractions, like Tulsa’s Downtown Arts District or the lake areas nearby, which offer steady, diverse visitor interest.

Nice lake.