There's a few other exceptions such as a tax lawyer, but I find that a lot of folks find comfort in just having me respond to any notices that they might get.

As @JonathanGreene said, tech has created an environment that allows folks like you Jon, to enjoy investing on your terms so that you do not put all of your eggs into one basket (so-to-speak).

Jaron Walling said something that caught my attention, "search for and buy a bad roof, leverage it during the negotiation"....especially of the property has been sitting on the market longer than normal for the current market, a "bad roof" might be a gift from the real estate genie.My point is this: get good at estimating and fixing a bad roof (or any particular problem found with most houses that sit on the market longer) and you'll get comfortable buying/fixing properties that scare off other buyers. 

But if you can find an investment that pushes out beyond the next 2 or 3 years into a  “different” financial environment you might have a better risk reward return. 

I have around 20-30k that I can let go of semi-comfortably and that can be enough in the small market.

Only in this way can they stand out in this ever-changing environment.

At least those are my observations.If you’re comfortable knowing the OOS risks, and still want to move forward, then great job, now you know what you’re getting into, which is part of due diligence.

That said, you have to be comfortable with your risk tolerance - are you going to keep yourself up at night? 

If there's a family member or friend in a similar situation, and you can both align on the initial plan (location, home type, price, usage/occupancy, etc) you can pretty easily get a co-ownership agreement in place and even a joint mortgage.The benefit here is it might open up your ability to buy a larger place in a nicer area which could lead to a faster rate of appreciation and overall better living environment. 

The lessons you learned the hard way in 2008 will be invaluable now, and it’s great that you’re aiming to stay small-scale and within your comfort zone of Sacramento, which gives you an advantage of knowledge in that market.Given your experience, I'd say start by focusing on three key areas to build confidence and minimize risks:Budget Control: Over-renovating was one of the big mistakes you mentioned.