Maybe a short sale.

How much did your homeowners insurance increase when you added short term rental to your policy?

i.e. you might save 50k by doing it yourself, but it might cost you 2500 or 4500/month in lost Short Term Rents, so you'll 'lose' a lot by not finishing fast.Just some things to think about.

To keep it short, I'll end it here in hopes of a good conversation.

I will be contacting my bank shortly to see if I can work with them to figure out a price range that I can work with for looking at a house as well as see if they have any agents.

I had about 80K in the stock market and sold it to pay cash for my condo.

My first property is $50 short from covering my whole mortgage and I replaced a few cap Ex items that I built into the contact that the seller paid for.

Jose,While there are many different benchmarks to compare an investment to in order to gauge success (excluding subjective meanings of success), an easy comparison is one made against the stock market (i.e.

I have a lot of confidence of on-going short-term rent appreciation (next 5 years) but less confidence of significant on-going property appreciation (I expect a leveling off but am not real confident of any prediction).High end homes (bigger and more expensive) have worse cash flow than middle class or working class homes.Note a small multiplex or your 16+ unit will experience similar rent and property appreciation to your SFR and have better initial cash flow (it will be poor initial cash for San Diego but increase with the rent appreciation).To summarize, SFR are not the best buy n hold investment option in San Diego. 

So that is where my journey started.I decided shortly after that to really take a look at my spending habits and see just exactly how I spent my money.