Items like a missing doorbell or blinds may fall into wear-and-tear depending on their age.

The ability to effectively self manage would depend on the scale you are trying to buy. 

I don't know that any of this would affect a new appraisal, but there may be some comments by the appraiser, which may or may not hurt you depending on why you want the appraisal in the first place. 

Ultimately though, it will depend on the lender and the availability of funds (assistance) available for the demographic area that you are purchasing in.Do you have a property that you are looking at?

The question is mostly a personal financial planning question and it depends on your preference and what balance of risk and access you'd like and would be comfortable with.

The amount depends on negotiations between you and the property owner. 

The structure will depend on the down payment, quality of borrower, terms of note, your cash out of the note sale needs, and other factors. 

This will vary depending on if a handyman can do the job or a licensed contractor is needed.

Never fully trust anyone that isn't willing to share the negative aspects of all this.As I'm sure you've experienced, this can be a very rewarding path to take and depending on your grit and determination, overcoming all the pitfalls are well worth the effort.Cheers and drive safe!

Depends on the area.