(Respectfully- Please don't tell me to save up and quit my job it's just not realistic for me and won't be anytime soon)If you read the threads on BP concerning wholesaling, you should be able to draw a few conclusions1. 99% of people trying wholesaling fail2.

What is drawing you to that specific location?

I was considering taking out a $240K HELOC with a 10-year draw period and pulling $160K from it to build the next rental property.

LTV Consideration – The 60%-70% LTV is usually based on the After-Repair Value (ARV), meaning your loan should be within that range relative to the projected value after renovations. 2.

HUD loans will take drastically longer (I've never used one personally), but there can be benefits to using these loans if you're a long-term owner.The interest rates in your Key Considerations seem very low for agency loans and they're definitely low for bridge loans. 

The advantage with the bank was minimal closing costs, a good interest rate, and a draw system so I could get funding as I completed each rental unit. 

There are state specific items to take into consideration.

Is there something I'm not taking into consideration?

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

This influx of high-paying jobs (averaging $60 per hour) is expected to draw a significant number of professionals to the area, boosting demand for housing and various services.