You'll see or understand something different every time.Due diligence....go to every single house you want to buy. 

I am not new in RE (Own 2 (condo+townhome) +primary home) and all units are in San Diego and know want to buy something near beach and been in Imperial Beach lot of times love the place :)Any guidance how should i approach?

So last week I did something truly dumb.

I agree SS is a bonus and not something to be overly reliant on.

So getting ownership over something in that context makes a great deal of sense, as long as the longer-term plan is to move out and rent out the property, rather than selling. 

This would create something that you already are familiar with, which then would lead you to be able to get into real estate as an investment vehicle.

If so, I would consider that route and redeploying the funds into a truly cash flowing property or a REIT or something.

Unfortunately, Prosper is refusing to cover without remedying the situation (at least a $1k in materials plus labor).I always want to fix any problems within my rental if they arise, but I don't want to replace something that is perfectly safe just to fit a policy.

That has to count for something.

@Ed Ma Why don't you just pull some money out of this property if your intention is to use it to invest in something else?