But, being a resident of California, there are lots of external factors you need to add to your overall analysis. 

In my LLC I have three checking accounts, one for external clients and two for separate product ventures.

When you don't have any silver hairs to add to your credibility, people will look to other external cues to judge you. 

@Hernan GuelmanYou should make an overall decision on whether to invest or not based on your return on the investment which factors external costs such as compliance fees that it would cost.Example = Projected annual return from investment $10,000Additional compliance cost as a result of investment $1,000Investment = $50,000return considering extra compliance costs = 18%return not considering extra compliance costs = 20%You should consult with your tax advisor just to see what the extra cost would be.

Hi, it seems that there are a lot of individuals that struggle to find the right investment property. For those looking to buy and hold without the renovation, outside of the turnkey sites like roof stock, is there a ...

I continued the repositioning by improving the externals of the building.

Painting is specifically interior paint job, not external.

Honestly, if you are worried about a repeat of your 2008 experience, I would NOT invest out of your sight, that way you keep eyes on your investment and can hand pick your tenants and spot issues right away. 

(exactly why I use phone.com and set the "do not disturb" from 8pm to 7am.... you MUST got to 24 hour emergency service, which is an external line to our PM's 24 hour line. :-)

History of profit / loss is just one of the tests the IRS will use in making this determination.Tax case law has established rentals can have a long and substantial history of tax loss and still be a trade or business...Highly encourage you to bring a tax CPA or EA onboard as one of your external team members.