I've got all of my ducks in a row (financing, agent, multiple potential deals).

It sounds like you've got a good handle on your property situation, but you're right to look for ways to minimize your tax hit from that nice appreciation you've seen.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

There's a lot more work involved in a rooming situation, so most managers won't touch it.

Normally I say you can find everyone, but many of the sellers were moved/retired out of the country, not easy access to notary, etc. or maybe the die and so that leaves the buyer in somewhat of a difficult situation to resolve.

So my question is... when running an analysis, should I get multiple estimates from general contractors during my first walk-through of the property or get estimates on my second walk-through?

My property manager is acting as the host and we have already had multiple bookings. 

I am currently in one beach market and multiple mountain markets.

Just looking for experiences or suggestions from others who have handled a similar situation. 

Multiple, billion dollar companies are investing substantial amounts of money into our area, such as Intel, Google, and Amazon.