@Jim Kennedy - Thanks for your words. It's true, I need to blaze my own trail :). I'd love to hear your 21-year plan. Let me know if we can connect sometime. I'm working hard every day to learn from my mistakes and finding my next property. I'll keep you posted :)
@Bob Norris - Thanks for your input. Because I don't own a property yet, I don't know how sellers feel about inspection reports. I read an analogy somewhere, it's like having an inspection report run on your car. You know your car has some miles on it and it runs super well, but the inspection report could say a million things about the car and you wouldn't even know the issues reported existed. So I try not to "beat up", but I ensure that the math makes sense going into the deal. I wouldn't want to spend $20k on a $200k property for repairs upfront.
@Chinmay J. - Thanks for your feedback. Will keep them in mind.
@Shawn Devoid - Ton of useful information in your reply. I'm educating myself on the forms and yes, Florida does require disclosing know deficiencies. Unfortunately, in my case, the property was managed poorly and the responses to questions like "Is the roof structurally sound and free of leaks" was "Yes", but there were issues with the roofs. So there wasn't much I could do there in spite of my due diligence. I can only get better at my due diligence with time and experience. Thanks for your note.
@Michael Haynes - Great perspective! I'll explore more on the tax-deferred investing. I want to buy a home for myself but I might not stay in the bay area over the next 5-7 years. So that changes plans of owning a home here.