Since I have been playing for a while and the industry is getting smaller due to regulations which reduces the traffic and the number of recreational players (which makes the game less profitable) I think is the moment to start transitioning to Real Estate.I am literally devorating everything in BP, just bought the 2 books of Brandon Turner (hey Brundon if you read this just let you know that I love the way you explain and the methods of teaching you follow, I really find them effective for newbies like me) so I will be trying to educate myself in RE as much as I can in order to be succesful in the future.If there is someone out there who is also starting in RE, in spanish market and want to connect me to talk about whatever or just for future networking, dont hesitate to do it!

What are the key market characteristics that I need to analyze to reduce the chances of owning property in a town that is dying fast?

You will earn your high yield from dealing with the tenants.  

Check out my first blog post in my profile, I actually was able to reduce my closing costs several thousand by doing this.

Ideally, you have the big 3 in place; your buying at a discount to retail, your confident you  CAN AND WILL  earn 2 for 1 dollars spent on improvements and #3, your buying in a market that is trending higher.

If you're not licensed, you can likely still cut some of the expenses by working an agreement with your realtor to receive full commission on the purchase of the property and a reduced fee on the flip (since your agent would get 2 commissions on one property, it's not unreasonable to ask them to take a small reduction on the back end of each one. 

If the majority are owner occupied, the board could change the bylaws to prevent or reduce future rentals.

The income on the 1099 is taxed an earned income so you'll pay federal and state income taxes as well as 15.3% towards self-employment tax.

I have a whole post about it.https://www.biggerpockets.com/forums/61/topics/364937-reducing-flood-insurance-costs?

However, when purchasing a home in the Bay Area with a median-ish earned income, I will need access to the first time home buyer benefits of lower down payments required and lower mortgage rates.