He had cash saved up for his first investment but was tempted to use a loan to “stretch” his money.

Other times they may quote something ridicules like $10k for painting because they're going to subcontract it and while I HATE painting it is something I can do for $100 and hour IF the budget is being stretched. 

As you mentioned they really take away the visibility from the street and roots could pose problems down the stretch.

My BIL had a neighbor survey a mile long stretch of farmland and said the “rock pile boundary” was off by 5-10+ feet over a mile, a few acres.

Nothing dilapidated by any stretch of the imagination.

Yes, you might have some stellar months as a STR during the year, but you might have long stretches where the property is vacant.

No HOAs at all.When I say afford, no more than 30% of your take home pay-- to stretch it 35% given you are in San Diego.

This woman might not be able to afford your apartment currently, some people might consider your apartment a steal of a price, and others will stretch their budget to be able to afford it.

It's just gonna be peppered in with more stretches of loss. 

Make sure that using your equity won’t leave you stretched thin, especially if property values fluctuate.Long-Term Strategy: Think about your long-term investment goals.