The thing I would be worried about is that these two properties will consume your entire life, you will have to overspend on both, you will overdo it on both because of the attachment and will end up with properties that are worth way more to you (emotionally) than to the open market.Your area has starkly rising insurance costs because of fires and the property in Carlsbad being near the water now has strong flood risk so your insurance and holding costs are going to keep going up and up which may hold down the overall value.

This is the forever debate... are gurus worth the money or not?  

You can kick that capex can down the road a couple years, but not forever

I’ve seen some long term options - as long as 25 years in one case, but it was concurrent with a triple net lease of the same length of time with the property being commercial.If the option is with a homeowner then you deal with consumer protection laws, Dodd Frank act, and CFPB.  

., Canada, and Mexico due to economic pressures on lower- and middle-income consumers.

Hey everyone,I’ve been working in real estate for a little bit now, and like many of you, I’ve found that two big challenges keep coming up:Finding distressed or off-market properties before they get picked up by others.The time-consuming process of property analysis—especially when trying to figure out ROI, ARV, or repair costs quickly.I’m curious how you all are dealing with these issues.

So we have a net deficit on housing stock that coincided with the millennials changing their mind on renting forever.

99.9% of lenders will not take a consumer ordered appraisal. 

Traditional Sales are too costly and time consuming. 4.

The former provides a much lower return on equity but is simpler and easy to achieve over the long run.The latter is much more time consuming and risky, but provides high returns and a lot of tax advantages.