For BRRRR i would stay away from New Western.

No other loan option comes close to that. 

If you opt for the second option, you’ll need to coordinate more closely with multiple subs, which could be time-consuming.It's crucial to have a team member overseeing the project, even if you choose one GC.

The student also got great experience and was able to stay in the deal over the long haul. 

Ultimately, the assigned appraiser was known for being extremely conservative, and the final valuation came in at $285,000, requiring an extra $10,000 out of pocket to close.After closing, I raised one tenant’s rent from $750 to $1,180, and they chose to stay.

It seems you and your husband have the ability to make a property more desirable and I would try to stay local for the same reasons you listed. 

Here are some key things to consider:Find a Sub-To Friendly Title Company or Attorney – Illinois is an attorney-close state, meaning real estate closings are typically handled by attorneys, not title companies.

They can provide training and help you close.

Hey BiggerPockets community,
 
Im a beginner wholesale real estate agent based in North Carolina, and I'm excited to dive into this game! I'm currently on the hunt for my first deal and eager to learn from all of you ...

I guess I should have stay the heck out of this one LOL