If things go sideways, you discovery greater rehab expenses, the market takes a turn for the worse, you can get in the red quickly. 

Quote from @Joshua Alcantara: I’m looking to move out of the current "red ocean" of real estate wholesaling and focus on helping sellers with problematic titles, such as liens, divorce issues, probate, quitclaim deeds, etc.All my previous high-value assignment fees came from working with sellers who inherited properties without a proper deed.

The benefit is significantly less red tape compared to working with your traditional local banks who also do new construction financing.

First red flag is if they say that they will shop your deal with a few different investors.  

.- Working a W2 as a firefighter, posting and consuming content- Leaving my W2 to dive deep into real estate investing and working as an agent... and still watching/posting content all while business was ok - Deleting social media apps (one have one on my phone that I use 10 minutes or less a day), diving deep into building my business and skills which have drastically increased due to pure focus and increasing my business significantly- moral of the story... focus on the things you need to do in business (dollar productive activities) and life experiences while reducing consumption will increase your success  

If you’re only getting 7 inquiries in 15 days with no applicants, that’s a red flag.

Additional Considerations: Costs & Market Changes•Ongoing Maintenance & Housekeeping: STRs require regular deep cleaning, restocking of supplies, and maintenance.

Buy some 5 gallon buckets with lids.Buy the following and store in buckets or 2 liter bottles.50 lb bag chickpea or garbanzo beans     50 black beans. 50 pinto beans.       50 rice50 Idaho potato50 red potato50 onions50 carrotsBulk pasta, or make it yourself(cheaper but a lot of work).Meat:Large spiral cut ham 20 lbPork tenderloin- 20 lb cut into boneless pork chops.Cheapest roast 20 lb.

If part of the property is rentable while renovations are happening, that could help offset carrying costs.Given your construction background, you’ve got a huge advantage in managing the project efficiently—it’s just about getting through the red tape and de-risking the unknowns before pulling the trigger.Have you talked to any local investors or contractors who’ve tackled similar projects in Wicker Park?

I'm a bit of a nomad who doesn't like to put roots down too deep ;)