After negotiating, we secured the property for $135,000, which was below market value, ensuring a strong margin for resale.

However, after reflection, I realized I was becoming too emotionally attached to my first investment after a 15-year break and faced challenges finding reliable contractors.Update (5/17/23):After three failed contractor attempts, I finally secured a reliable one.

Recently, I was lucky to sign a deal using an option agreement like Seller's finance, when you pay an Option fee, secure a deal for a couple of years, and do not pay the down payment.

You are making a grave mistake by looking too far ahead right now, without capital, because that usually means you aren't focused on upgrading and securing your first asset.

From what I understand, it's designed to replace a traditional security deposit.

An STR will look every bit as good as it did when it started - because it has to.Not only that but it is much easier for property managers to get repairs reimbursed when a guest damages something as an STR as opposed to when a long term renter moves out and outside of the security deposit, good luck. 

We're considering using an FHA loan, but due to his credit score, we haven't started the preapproval process yet.What steps would you recommend we take to secure funding for our first investment?

I copied this from the Chicago RTLO which is attached to the CAR lease:-Before a landlord can deduct expenses for damages from the security deposit, the landlord must provide the tenant with an itemized statement of the damages within 30 days of the date the tenant vacates the dwelling unit.

My current focus is on securing my first deal under contract using PropStream & Off-Market strategies I am eager to connect with experienced investors who can provide insights or advice to help me navigate the early stages of my real estate journey.

That you can secure CONTROL and MONITIZATION of a property via a fractional capital outlay vs it's market value, better known as a down payment.