I've been constantly in search of ways to make this happen.

I would say that appreciation will continue to rise at a constant pace in San Jose.

stucco is not particularly water proof and will fail quickly if not properly installed.Typically we lay down a heavier stucco specific house wrap and even then I am constantly worried about the stuff. 

The constant gloomy and wet weather is so depressing.

Or the possible settling issues from the constant drillings.

Over the past 5 years my avg income has been over 6 figures and I think going forward I can most likely save 60-80k year for investing(as long as the economy and the lobster population remain constant). 

Anything less and you’re dealing with part time workers who will constantly be coming and going which makes things much more difficult to manage* You are the average of the 5 people you spend the most time with — level yourself up.

I'm of the opinion that there's nothing wrong with making money and there's nothing wrong with a company getting profit if they are offering value - and in our case the overriding considerations we have used to justify this decision are that:We should be doing something more valuable with our time than handling service calls (and we have those opportunities in the hopper)We have higher 'costs' (lets call them transactional costs) associated with constantly trying to maintain a network of competent service suppliers. 

These are control able through education,  discipline,  and insurance.Your best method of prevention for going bankrupt is to constantly be learning, have equity in your properties (or use all cash, yours or someone else's) and some multiple of monthly expenses in the bank at all times to cover stuff that comes up.

I am constantly looking at deals and I have been stuck in analysis paralysis a bit.