This strategy will only help to support your value in your farm and sphere.I also highly recommend door-knocking and dropping off a flyer or door-hanger, as opposed to putting all of your eggs in the direct mail basket.From an investor perspective, I know investors who have done direct mail have had some limited success by offering "all cash" for distressed properties.

I have tried to get as much information as possible to understand at what point the market is in but i'm getting everything from "Danger- SF bay area is on the brink of the next tech bubble crash" to "Safe- because of the amount of capitol available in the bay area the market is really only overvalued by 10% as opposed to a real bubble market which is overvalued much higher"I see that the multi-families available are definitely retail post flip prices, especially in the areas I would consider living in with a baby and many of those have rent controlled tenants.I'm trying to think creatively about moving forward weighing our $30,000 annual rent bill against potentially having a $600,000-$800,000 mortgage in a single 4 plex where it seems to make sense financial now but I'm concerned about market crash or unforeseen event.I guess my question is what would you do, invest elsewhere and stay put with high rent or dive into a bay area house hack?

They will have some strict guidelines in terms of exterior preservation. 

I have thought of that but timing is everything so it will take much longer to fund a conventional loan opposed to hard money.

Despite the rain we had in Houston recently, I managed to get the exterior repair completed.

Getting a HELOC, as opposed to actually refinancing, while you are an owner occupant of the duplex, and still going FHA on your next purchase?  

We are reaching out to him to explore just what you mention - retaining the exterior facade and incorporating enough to the interior - particularly the trompe l'oeil - to pay respect to the history of the building.Senior living is an avenue we are exploring, but might be cost prohibitive if an elevator need be incorporated.We dismissed B&B - the property would be fitting, but they are in abundance already and some of the older, more established ones are struggling these days.If it wasn't for the fact we have real winters here and 6500 ft^2 of this age costs ~10-12K to heat - we could experiment with less risk.The purchasing of this property will undoubtedly be the least costly aspect of a deal.

I am not opposed to wholesaling it if I cant find financing, but this is one I really want to put a stamp on. 

I am doing to property management for now.It is not appreciation based, but that is what takes most of the risk of the buying decision here for me.The monthly expenses that I am calculating are:Gas & Electric: $100, for exterior lights and water heater.Water: Individually metered units, tenants responsibilityGarbage is taken care of by the city out of the property taxesMaintenance: $250 because of the condition of the property and warranties in place.

Trevor, I enjoy the work and i do think it becomes a risk vs. reward issue as opposed to a like/ dislike.