One downside is that depending on your state and sponsoring broker you will have to disclose your status as an agent plus even be required to pay for home warranty on your personal sales. 

A good lender for reference, who is active on here, would be either @Diana Muresan , @Chris Mason or at @Andrew Postell .I'm sure one of them will be able to validate whether any concern is needed with the strategy you mentioned. 

For example, if you buy a home and transfer it into an LLC where you are the owner the title insurance should still be valid but if another person takes over a deed, title insurance needs to be rebought.That is how it can work in NJ at least I think.

The contractor that did the inspections didn’t even mentioned the warranty or type if roof I will get.

Make sure you’re taking the high ground, and if they do provide you valid receipts for valid damages, then you should pay.

I'm not going to knock your education, but I think the questions you are asking are very valid.They are so valid that I feel that SJSU should be teaching their graduates this sort of information. 

This will look terrible and likely void the warranty.

You have a few options, which depend on a number of factors, including whether there is a valid lease agreement with a remaining term, how long the tenants have lived in the property, whether they are still paying rent, the city that the property is in, and whether any city ordinances apply to the property. 

Hopefully you are writing them down ... and will be validating them... 

Their are many in the area to choose from so research and interview the ones that are closest to your property once you make your first purchase.I understand you are at the beginning stages so your questions are very valid but require way more than a one sentence answer.