Creative Freedom: You get to design and transform spaces, which can be personally fulfilling.The Bad: Where Flippers Lose Money⚠️ Underestimating Repair Costs: Surprise structural issues, contractor delays, and material price spikes can kill your budget.⚠️ Market Changes: A hot market today might cool down before you sell, which reduces the profit.⚠️ Financing Challenges: Hard money loans carry high interest rates that nibble into the bottom line.Unrealistic timelines: If you think you're going to be in and out in 60 days, you're sadly mistaken-most flips take longer than expected.Real Talk: Is Fix and Flip Still Worth It?

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

@Ben Syzek with $50k, you're probably looking at a property with a total cost (purchase price + reno) around $250k.

The instruments needed for the transaction will be state specific which means you should have someone from California chime in with resources who can provide low cost documents (as these will be boiler plate).

Streamlining Renovations for Efficiency & Cost ControlManaging multiple renovation projects at once demands an operational efficiency that can be tough to achieve.

Evaluate Property ConditionOlder Chicago buildings often have charm—but may come with hidden costs.

Aloha Joshua,  I deal with clouded/messy titles often and it's not my first choice as its froth with a lot of time, costs and risks. 

Focus on key areas first (like floors, walls, kitchen, or bathroom), which may help you handle the costs more gradually, even if it means moving in furniture or updating fixtures down the line.Also, since the tenant left it in rough shape, be sure to document all the damage (photos, receipts) in case you decide to pursue reimbursement through their security deposit or in court.

However, the property’s cost basis (what they originally paid) carries over to you, meaning if you later sell, you may owe significant capital gains tax on appreciation.Alternatively, selling the property at fair market value eliminates gift tax concerns, but your in-laws may owe capital gains tax on any profit.

With that, you could cover the costs for renovations, closing costs, or even set up escrow for those senior living sponsorships.