The person I would seek advice from is a CPA about this. 

That's just my personal way of really feeling like I've comprehended the topics rather than just listened to them. 2.

Don't talk yourself into a place because of personal use.Buying a $475k condo that brings in 35k in gross rental income will lose a lot of money.

If the person stops making payments, they alas,  have to foreclose.

Not sure if they have upgraded to desktop appraisals but if they are still doing in person appraisals , make sure you get everything (scope of work, good faith deposit, social, LLC docs, insurance, proof of prior experience, financial statements) in ASAP.

The vast majority of contractors won't want to give bids on properties while under contract unless they have a relationship with that person from prior jobs.

In person is better than over the phone if possible, as I have been told by annoyed or lazy clerks "NO STR allowed" as that was the easy button to get me off the phone, or if they are anti STR. 

The question is, what is the intention  of the owner, not what would a reasonable person think is the intention of the owner.

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

You must have your personal finances in order before you invest.