If I buy a single family home with a conventional mortgage and 5% down, I'll have enough left over to eventually buy another property if owner occupy it and use an FHA loan.

But we have clients who have converted their properties from annual to STR and have made significantly more income. 

I wonder if it was a single family converted to multiple?

We converted the detached garage into a 2 bedroom rental to "house-hack" and minimize our living expenses in this expensive part of the Bay Area.

I would like to take the profits and purchase vacant land to be used eventually as Home/Airbnb.

Purchase price: $183,400 Converting historic duplex to single-family home w/ 4 BD, 3 BA.

There are some positives though: after looking at the market, I'm pretty convinced that I made a good choice to buy this property if I eventually succeed in fixing this foundation.

With propane prices being so high, i'm trying to convert to as much electrical as I can, with potential future hopes to get some solar panels as well. 

There are a few ways to go about it:Find a house in your price range with as many rooms as possible and rent out all the roomsRepeat option one but find a house that could be converted into two units - you occupy one unit and rent out the other unitIf you can find a house to convert into two units, you might want to look into the short-term rental rules in your area to increase your cashflow even more :) 

Anyone can eventually do a deal, the key is how to do deals consistently.