Between what I expected to earn that year and the support I was granted in my mediation agreement, I could not afford to rent, much less purchase, a 2-bedroom condo in Oakland, California, where I planned to move after raising my children in a suburb half an hour away.Dad to the rescue!

With regards to the structural issues and really any other noticeable property defects, if something is visible and obvious on the initial viewing then you should not expect additional price reduction after inspection. 

Make sure you know what that particular street in that particular neighborhood expects as far as quality and materials, and meet those standards.

When a guest has one review and a host has 30 5 star review 6 months and have only asked for damages twice....I do expect to have to prove my side, but when photos and the next unrelated guests confirms my side, but my claim is denied because the invoice doesn't meet their standards?

@Ruel BaliongIf you are a first-time flipper, I'd expect about 12% interest, 3-4 pts, and 20% down payment.If you're a seasoned flipper, I've seen as low as 8%, 1.5 pts, and 10% down on purchase price with 100% rehab financing.

The average rental in that area actually little bit lower than you expected, plus the turn over rate is higher as well due to tenants creditability.

Unfortunately, the deposit funds were never transferred to me because the management company was forced to close (they also owe me thousands in collected rent that I don't expect to see). 

When should I expect the winter season tenets to start calling?

I'm having my resume rewritten but don't expect to earn more than $35k at a regular job (but I need some decent health insurance).

That is my understanding about security deposits.In the future though I do not think it is realistic to expect tenants to maintain flower beds.